Fungicidal N,N&#39;-diacylaminals

ABSTRACT

Fungicidal N,N&#39;-diacylaminals of the formula ##STR1## in which R 1  is optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl or cycloalkenyl, 
     R 2  and R 3  are hydrogen or various organic radicals, and 
     X is oxygen or sulphur.

The present invention relates to new N,N'-diacylaminals, severalprocesses for their preparation, and their use in pesticides, inparticular as fungicides.

It has already been disclosed that certain substituted2-cyano-2-oximino-acetamides have a good fungicidal activity (cf., forexample, EP-OS (European Published Specification) 0,201,999 and DE-OS(German Published Specification) 3,602,243). However, the action ofthese compounds is not always fully satisfactory, in particular at lowapplication rates and concentrations.

New N,N'-diacylaminals of the general formula (I) ##STR2## in which R¹stands for optionally substituted alkyl having the followingsubstituents: halogen, cyano, --COOR^(I), --CONR^(II) R^(III),--OR^(IV), acyl, optionally substituted aryl, optionally substitutedcycloalkyl or optionally substituted heterocyclyl; R¹ furthermore standsfor in each case optionally substituted alkenyl or alkinyl, or for ineach case optionally substituted cycloalkyl or cycloalkenyl,

R² stands for hydrogen or for optionally substituted alkyl having thefollowing substituents: cyano, alkoxy, alkylthio, --COOR^(I), acylamino,optionally substituted aryl, optionally substituted cycloalkyl oroptionally substituted heterocyclyl; R² furthermore stands for in eachcase optionally substituted alkenyl or alkinyl, for in each caseoptionally substituted cycloalkyl or cycloalkenyl, for optionallysubstituted aryl or for optionally substituted heterocyclyl,

R³ stands for hydrogen or for optionally substituted alkyl having thefollowing substituents: halogen, alkoxy, alkylthio, alkylsulphinyl,alkylsulphonyl, acyloxy, acylamino, cyano, --COOR^(I), optionallysubstituted aryl, optionally substituted cycloalkyl or optionallysubstituted heterocyclyl; R³ furthermore stands for in each caseoptionally substituted alkenyl or alkinyl; R³ additionally stands for ineach case optionally bridged and/or fused, in each case optionallysubstituted cycloalkyl or cycloalkenyl; R³ in addition stands foroptionally fused, optionally substituted aryl or optionally fused,optionally substituted heterocyclyl, or furthermore for alkoxycarbonyl,--OR⁴, --SR⁴ or --NR⁵ R⁶, stands for optionally substituted alkyl havingthe following substituents: halogen, --OR^(IV), --SR^(IV), --COOR^(I),--CONR^(II) R^(III), --CN, --NR^(II) R^(III), acyl, in each caseoptionally substituted aryl or aryloxy, in each case optionallysubstituted cycloalkyl or cycloalkenyl, or optionally substitutedheterocyclyl; R⁴ furthermore stands for in each case optionallysubstituted alkenyl or alkinyl, or furthermore for in each caseoptionally substituted cycloalkyl or cycloalkenyl,

R⁵ stands for hydrogen or for optionally substituted alkyl having thefollowing substituents: halogen, cyano, --COOR^(I), --CONR^(II) R^(III),--NR^(II) R^(III), --OR^(IV), --S(O)_(n) R^(IV), acyl, or in each caseoptionally substituted aryl, heterocyclyl, cycloalkyl or cycloalkenyl;R⁵ furthermore stands for in each case optionally substituted alkenyl,alkinyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl, and

R⁶ stands for hydrogen or for optionally substituted alkyl having thefollowing substituents: halogen, cyano, --COOR^(I), --CONR^(II) R^(III),--NR^(II) R^(III), --OR^(IV), --S(O)_(n) R^(IV), acyl, or in each caseoptionally substituted aryl, heterocyclyl, cycloalkyl or cycloalkenyl;or R⁶ furthermore stands for in each case optionally substitutedalkenyl, alkinyl, cycloalkyl, cycloalkenyl, aryl, heterocyclyl or the--OR^(IV) group, or

R⁵ and R⁶, together with the nitrogen atom to which they are bonded,stand for an optionally substituted heterocyclic ring which may containfurther hetero atoms,

R^(I) stands for hydrogen or optionally substituted alkyl having thefollowing substituents: halogen, or in each case optionally substitutedaryl, cycloalkyl or cycloalkenyl,

R^(II) and R^(III) are identical or different and stand for hydrogen oroptionally substituted alkyl having the following substituents: halogen,--COOR^(IV), --CONR^(I) R^(IV), or in each case optionally substitutedaryl, cycloalkyl or cycloalkenyl; or R^(II) and R^(III) furthermorestand for alkenyl, alkinyl, or in each case optionally substitutedcycloalkyl, cycloalkenyl, aryl or heterocyclyl, or, together with thenitrogen atom to which they are bonded, stand for an optionallysubstituted heterocyclic ring which may contain further hetero atoms,

R^(IV) stands for hydrogen, alkyl, aralkyl or acyl,

n stands for the numbers 0, 1 or 2, and

X stands for oxygen or sulphur,

have now been found.

The compounds of the formula (I) can exist in various geometricalisomers, depending on the arrangement of the substituents on the C═Ngroup (E- or Z-isomers).

The compounds may have one or more asymmeytrical carbon atoms; they canthus also exist as enantiomers or diastereomers, which can be producedin various amount ratios. They are predominantly produced as racemates.

It has furthermore been found that the new N,N'-diacylaminals of thegeneral formula (I) ##STR3## in which R¹ stands for optionallysubstituted alkyl having the following substituents: halogen, cyano,--COOR^(I), --CONR^(II) R^(III), --OR^(IV), acyl, optionally substitutedaryl, optionally substituted cycloalkyl or optionally substitutedheterocyclyl; R¹ furthermore stands for in each case optionallysubstituted alkenyl or alkinyl, or for in each case optionallysubstituted cycloalkyl or cycloalkenyl,

R² stands for hydrogen or for optionally substituted alkyl having thefollowing substituents: cyano, alkoxy, alkylthio, --COOR^(I), acylamino,optionally substituted aryl, optionally substituted cycloalkyl oroptionally substituted heterocyclyl; R² furthermore stands for in eachcase optionally substituted alkenyl or alkinyl, for in each caseoptionally substituted cycloalkyl or cycloalkenyl, for optionallysubstituted aryl or for optionally substituted heterocyclyl,

R³ stands for hydrogen or for optionally substituted alkyl having thefollowing substituents: halogen, alkoxy, alkylthio, alkylsulphinyl,alkylsulphonyl, acyloxy, acylamino, cyano, --COOR^(I), optionallysubstituted aryl, optionally substituted cycloalkyl or optionallysubstituted heterocyclyl; R³ furthermore stands for in each caseoptionally substituted alkenyl or alkinyl; R³ additionally stands for ineach case optionally bridged and/or fused, in each case optionallysubstituted cycloalkyl or cycloalkenyl; R³ in addition stands foroptionally fused, optionally substituted aryl or optionally fused,optionally substituted heterocyclyl, or furthermore for alkoxycarbonyl,--OR⁴, --SR⁴ or --NR⁵ R⁶,

R⁴ stands for optionally substituted alkyl having the followingsubstituents: halogen, --OR^(IV), --SR^(IV), --COOR^(I), --CONR^(II)R^(III), --CN, --NR^(II) R^(III), acyl, in each case optionallysubstituted aryl or aryloxy, in each case optionally substitutedcycloalkyl or cycloalkenyl, or optionally substituted heterocyclyl; R⁴furthermore stands for in each case optionally substituted alkenyl oralkinyl, or furthermore for in each case optionally substitutedcycloalkyl or cycloalkenyl,

R⁵ stands for hydrogen or for optionally substituted alkyl having thefollowing substituents: halogen, cyano, --COOR^(I), --CONR^(II) R^(III),--NR^(II) R^(III), --OR^(IV), --S(O)_(n) R^(IV), acyl, or in each caseoptionally substituted aryl, heterocyclyl, cycloalkyl or cycloalkenyl;R⁵ furthermore stands for in each case optionally substituted alkenyl,alkinyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl, and

R⁶ stands for hydrogen or for optionally substituted alkyl having thefollowing substituents: halogen, cyano, --COOR^(I), --CONR^(II) R^(III),--NR^(II) R^(III), --OR^(IV), --S(O)_(n) R^(IV), acyl, or in each caseoptionally substituted aryl, heterocyclyl, cycloalkyl or cycloalkenyl;or R⁶ furthermore stands for in each case optionally substitutedalkenyl, alkinyl, cycloalkyl, cycloalkenyl, aryl, heterocyclyl or the--OR^(IV) group,

R⁵ and R⁶, together with the nitrogen atom to which they are bonded,stand for an optionally substituted heterocyclic ring which may containfurther hetero atoms,

R^(I) stands for hydrogen or optionally substituted alkyl having thefollowing substituents: halogen, or in each case optionally substitutedaryl, cycloalkyl or cycloalkenyl,

R^(II) and R^(III) are identical or different and stand for hydrogen oroptionally substituted alkyl having the following substituents: halogen,--COOR^(IV), --CONR^(I) R^(IV), or in each case optionally substitutedaryl, cycloalkyl or cycloalkenyl; or R^(II) and R^(III) furthermorestand for alkenyl, alkinyl, or in each case optionally substitutedcycloalkyl, cycloalkenyl, aryl or heterocyclyl, or, together with thenitrogen atom to which they are bonded, stand for an optionallysubstituted heterocyclic ring which may contain further hetero atoms,

R^(IV) stands for hydrogen, alkyl, aralkyl or acyl,

n stands for the numbers 0, 1 or 2, and

X stands for oxygen or sulphur,

are obtained when

(a) N-(2-cyano-2-oximino-acetyl)-aminals of the formula (II) ##STR4## inwhich R¹ and R² have the abovementioned meaning, and

HY stands for the equivalent of an inorganic or organic acid,

are reacted with an acylating reagent of the formula (IIIa) or (IIIb)

    Z--CX--R.sup.3                                             (IIIa)

or

    X═C═N--R.sup.6                                     (IIIb)

in which

Z stands for a customary leaving group, such as halogen, --O--CO--R³,--O--CO--OR⁴, --OR⁴, --SR⁴, carboxymethoxy or carboxymethylthio, and

R³, R⁴, R⁶ and X have the abovementioned meaning, if appropriate in thepresence of a base and in the presence of a diluent and if appropriatein the presence of a catalyst;

or

(b) isocyanates of the formula (IV) ##STR5## in which R¹ and R² have theabovementioned meaning, are reacted with a protic nucleophile of theformula (Va) or (Vb)

    HO--CO--R.sup.3                                            (Va)

or

    H--R.sup.7                                                 (Vb)

in which

R⁷ stands for --OR⁴, --SR⁴ or --NR⁵ R⁶, and

R³, R⁴, R⁵ and R⁶ have the abovementioned meaning,

in the presence of a diluent and if appropriate in the presence of acatalyst.

Finally, it has been found that the new N,N'-diacylaminals have strongfungicidal properites, inter alia. In this respect, the compoundsaccording to the invention surprisingly exhibit a stronger action thanthe substituted 2-cyano-2-oximino-acetamides known from the prior art,which are similar compounds constitutionally or regarding their action.The substances according to the invention thus represent an enrichmentof the art.

In the text below, all aliphatic radicals, such as alkyl, alkoxy,alkenyl, etc., alone or in combinations, such as alkoxyalkyl, may bestraight-chain or branched, and in addition the aliphatic radicals maygenerally be substituted by identical or different substituents,preferably monosubstituted to pentasubstituted, particularly preferablymonosubstituted, disubstituted or trisubstituted, or very particularlypreferably monosubstituted or disubstituted; likewise, all ring systemsare optionally monosubstituted to pentasubstituted by identical ordifferent substituents, particularly preferably monosubstituted,disubstituted or trisubstituted, or very particularly preferablymonosubstituted or disubstituted, unless otherwise stated or notexpressly described.

Formula (I) provides a general definition of the N,N'-diacylaminalsaccording to the invention. In this formula (I),

R¹ preferably stands for straight-chain or branched alkyl having 1 to 6carbon atoms which is optionally monosubstituted to pentasubstituted byidentical or different substituents, the following substituents beingsuitable: fluorine, chlorine, bromine, iodine, cyano, --COOR^(I),--CONR^(II) R^(III), --OR^(IV), acyl having 2 to 9 carbon atoms, phenylwhich is optionally monosubstituted to pentasubstituted by identical ordifferent substituents, phenyl substituents which may be mentionedbeing: halogen, alkyl and alkoxy each having 1 to 4 carbon atoms,halogenoalkyl and halogenoalkoxy each having 1 to 2 carbon atoms and 1to 5 identical or different halogen atoms; further alkyl substituentsare cycloalkyl having 3 to 6 carbon atoms which is optionallymonosubstituted to pentasubstituted by identical or different alkylhaving 1 to 4 carbon atoms, and 3- to 6-membered heterocyclyl having 1to 3 identical or different hetero atoms, such as nitrogen, oxygen andsulphur atoms, which is optionally monosubstituted to pentasubstitutedby identical or different substituents from the series comprisinghalogen and alkyl having 1 to 4 carbon atoms; R¹ furthermore preferablystands for straight-chain or branched alkenyl or alkinyl, each of whichhas 2 to 6 carbon atoms and is optionally monosubstituted, disubstitutedor trisubstituted by identical or different substituents, substituentswhich may be mentioned being: phenyl which is optionally monosubstitutedto pentasubstituted by identical or different substituents from theseries comprising halogen and alkyl having 1 to 4 carbon atoms; R¹ inaddition preferably stands for cycloalkyl having 3 to 6 carbon atoms orcycloalkenyl having 5 to 7 carbon atoms, each of which is optionallymonosubstituted to pentasubstituted by identical or different alkylhaving 1 to 4 carbon atoms;

R² preferably stands for hydrogen or straight-chain or branched alkylhaving 1 to 6 carbon atoms which is optionally monosubstituted topentasubstituted by identical or different substituents, suitable beingthe following: cyano, alkoxy and alkylthio, each having 1 to 4 carbonatoms, --COOR^(I), acylamino having 2 to 9 carbon atoms, phenyl which isoptionally monosubstituted to pentasubstituted by identical or differentsubstituents, suitable substituents being the phenyl substituentsmentioned above as preferred in the case of R¹ ; further alkylsubstituents are cycloalkyl having 3 to 6 carbon atoms which isoptionally monosubstituted to pentasubstituted by identical or differentalkyl having 1 to 4 carbon atoms, and 3- to 6-membered heterocyclylhaving 1 to 3 identical or different hetero atoms, such as nitrogen,oxygen and sulphur atoms, which is optionally monosubstituted topentasubstituted by identical or different substituents from the seriescomprising halogen and alkyl having 1 to 4 carbon atoms; R² furthermorepreferably stands for straight-chain or branched alkenyl or alkinyl,each of which has to 6 carbon atoms and is optionally monosubstituted,disubstituted or trisubstituted by identical or different substituents,substituents which may be mentioned being: phenyl which is optionallymonosubstituted to pentasubstituted by identical or differentsubstituents from the series comprising halogen and alkyl having 1 to 4carbon atoms; R² in addition preferably stands for cycloalkyl having 3to 6 carbon atoms or cycloalkenyl having 5 to 7 carbon atoms, each ofwhich is optionally monosubstituted to pentasubstituted by identical ordifferent alkyl having 1 to 4 carbon atoms; R² additionally preferablystands for phenyl which is optionally monosubstituted topentasubstituted by identical or different substituents, suitablesubstituents being the phenyl substituents mentioned above as preferredin the case of R¹ ; R² furthermore preferably stands for 3- or6-membered heterocyclyl having 1 to 3 identical or different heteroatoms, such as nitrogen, oxygen and sulphur atoms, which is optionallymonosubstituted to pentasubstituted by identical or differentsubstituents from the series comprising halogen and alkyl having 1 to 4carbon atoms;

R³ preferably represents hydrogen or straight-chain or branched alkylhaving 1 to 6 carbon atoms which is optionally monosubstituted topentasubstituted by identical or different substituents, suitablesubstituents being the following: fluorine, chlorine, bromine, iodine,cyano, alkoxy, alkylthio, alkylsulphinyl and alkylsulphonyl each having1 to 4 carbon atoms, acyloxy and acylamino each having 2 to 9 carbonatoms, --COOR^(I), phenyl which is optionally monosubstituted topentasubstituted by identical or different substituents, suitablesubstituents being the phenyl substituents mentioned above as preferredin the case of R¹ ; further alkyl substituents are cycloalkyl having 3to 6 carbon atoms which is optionally monosubstituted topentasubstituted by identical or different alkyl having 1 to 4 carbonatoms, and 3- to 6-membered heterocyclyl having 1 to 3 identical ordifferent hetero atoms, such as nitrogen, oxygen and sulphur atoms,which is optionally monosubstituted to pentasubstituted by identical ordifferent substituents from the series comprising halogen and alkylhaving 1 to 4 carbon atoms; R³ furthermore preferably stands forstraight-chain or branched alkenyl or alkinyl, each of which has 2 to 6carbon atoms and is optionally monosubstituted, disubstituted ortrisubstituted by identical or different substituents, substituentswhich may be mentioned being: phenyl which is optionally monosubstitutedto pentasubstituted by identical or different substituents from theseries comprising halogen and alkyl having 1 to 4 carbon atoms; R³furthermore preferably stands for cycloalkyl having 3 to 6 carbon atomsor cycloalkenyl having 5 to 7 carbon atoms, each of which is optionallybridged by methylene or ethylene and/or fused to 1 or 2 benzene,cyclopentane or cyclohexane rings and is optionally monosubstituted topentasubstituted by identical or different substituents, substituentswhich may be mentioned being: halogen, alkyl and alkoxy each having 1 to4 carbon atoms, acyloxy and acylamino each having 2 to 5 carbon atoms,the oxo group, phenyl, hydroxycarbonyl and alkoxycarbonyl having 1 to 4carbon atoms in the alkoxy part; R³ in addition preferably stands forphenyl which is optionally fused to 1 or 2 benzene or cyclohexane ringsand is optionally substituted or pentasubstituted by identical ordifferent substituents, substituents which may be mentioned being:halogen, hydroxyl, nitro, alkyl and alkoxy each having 1 to 4 carbonatoms, halogenalkyl and halogenoalkoxy each having 1 or 2 carbon atomsand 2 to 5 identical or different halogen atoms, such as fluorine andchlorine atoms, acylamino and acylalkylamino each having 2 to 5 carbonatoms in the acyl part and 1 to 4 carbon atoms in the alkyl part,hydroxycarbonyl and alkoxycarbonyl having 1 to 4 carbon atoms in thealkoxy part;

R³ furthermore preferably stands for 5- or 6-membered heterocyclylhaving 1 to 3 identical or different hetero atoms, such as nitrogen,oxygen and sulphur atoms, which is optionally fused to 1 or 2 benzene,cyclopentane or cyclohexane rings and is optionally monosubstituted topentasubstituted by identical or different substituents, substituentswhich may be mentioned being: halogen, alkyl having 1 to 4 carbon atoms,acyl having 2 to 9 carbon atoms, phenyl, the oxo group and hydroxyl;finally, R³ alternatively preferably stands for alkoxycarbonyl having 1to 4 carbon atoms in the alkoxy part, or for --OR⁴, --SR⁴ or --NR⁵ R⁶ ;

R⁴ preferably stands for straight-chain or branched alkyl having 1 to 6carbon atoms which is optionally monosubstituted to pentasubstituted byidentical or different substituents, suitable substituents being thefollowing: halogen, --OR^(IV), --SR^(IV), --COOR^(I), --CONR^(II)R^(III), CN, --NR^(II) R^(III), acryl having 2 to 9 carbon atoms, phenylor phenoxy, each of which is optionally monosubstituted topentasubstituted by identical or different substituents from the seriescomprising halogen and alkyl having 1 to 4 carbon atoms, cycloalkylhaving 3 to 6 carbon atoms or cycloalkenyl having 5 to 7 carbon atoms,each of which is optionally monosubstituted to pentasubstituted byidentical or different alkyl having 1 to 4 carbon atoms, and 3- to6-membered heterocyclyl having 1 to 3 identical or different heteroatoms, such as nitrogen, oxygen and sulphur atoms, which is optionallymonosubstituted or pentasubstituted by identical or differentsubstituents from the series comprising halogen and alkyl having 1 to 4carbon atoms; R⁴ furthermore preferably stands for alkenyl or alkinyleach having 2 to 6 carbon atoms, or for cycloalkyl having 3 to 6 carbonatoms or cycloalkenyl having 5 to 7 carbon atoms, each of which isoptionally monosubstituted to pentasubstituted by identical or differentalkyl having 1 to 4 carbon atoms;

preferably stands for hydrogen or for straight-chain or branched alkylhaving 1 to 4 carbon atoms which is optionally monosubstituted ordisubstituted by identical or different substituents, substituents whichmay preferably be mentioned being: halogen, cyano, --COOR^(I),--CONR^(II) R^(III), --NR^(II) R^(III), --OR^(IV), --S(O)_(n) R^(IV),acyl having 2 to 9 carbon atoms, phenyl which is optionallymonosubstituted to pentasubstituted by identical or differentsubstituents from the series comprising halogen and alkyl having 1 to 4carbon atoms, a 5- or 6-membered heterocyclic ring having 1 to 3identical or different hetero atoms, for example nitrogen, oxygen andsulphur, which is optionally monosubstituted or pentasubstituted byidentical or different substituents from the series comprising halogen,alkyl and alkoxy each having 1 to 4 carbon atoms, or cycloalkyl having 3to 6 carbon atoms or cycloalkenyl having 5 to 7 carbon atoms, each ofwhich is optionally monosubstituted to pentasubstituted by identical ordifferent alkyl having 1 to 4 carbon atoms; R⁵ furthermore preferablystands for straight-chain or branched alkenyl or alkinyl each having 2to 6 carbon atoms; for cycloalkenyl having 5 to 7 carbon atoms which isoptionally monosubstituted or pentasubstituted by identical or differentalkyl having 1 to 4 carbon atoms, or for cycloalkyl having 3 to 6 carbonatoms which is optionally monosubstituted to pentasubstituted byidentical or different substituents, substituents which may preferablybe mentioned being: halogen, alkyl and alkoxy each having 1 to 4 carbonatoms, cyano, amino, carbamoyl, alkylamino, dialkylamino, alkylcarbamoyland dialkylcarbamoyl each having 1 to 4 carbon atoms in each alkyl part,alkoxycarbonylamino having 1 to 4 carbon atoms in the alkoxy part,cycloalkyl and cycloalkylalkyl having 5 or 6 carbon atoms in thecycloalkyl part and 1 to 4 carbon atoms in the straight-chain orbranched alkyl part, or phenyl or pyrrolidone each of which isoptionally monosubstituted to pentasubstituted by identical or differentsubstituents from the series comprising halogen and alkyl having 1 to 4carbon atoms; R⁵ additionally preferably stands for phenyl which isoptionally monosubstituted to pentasubstituted by identical or differentsubstituents from the series comprising halogen, alkyl or alkoxy eachhaving 1 to 4 carbon atoms, or halogenoalkyl or halogenoalkoxy eachhaving 1 to 2 carbon atoms and 1 to 5 identical or different halogenatoms, or for a 5- or 6-membered heterocyclic ring having 1 to 3identical or different hetero atoms, such as, in particular, nitrogen,oxygen and sulphur atoms, which is optionally monosubstituted topentasubstituted by identical or different substituents; substituentswhich may be mentioned being halogen, mercapto, phenyl, straight-chainor branched alkyl, alkoxy, alkylthio, alkylsulphinyl and alkylsulphonylhaving 1 to 4 carbon atoms in each alkyl part;

R⁶ preferably stands for the meanings of R⁵ or the --OR^(IV) group;

or

R⁵ or R⁶, together with the nitrogen atom to which they are bonded,preferably stand for a monocyclic, bicyclic or tricyclic heterocyclicring or spiroheterocyclic ring having 1 to 3 further identical ordifferent hetero atoms, such as oxygen, nitrogen or sulphur atoms, whichis optionally monosubstituted to pentasubstituted by identical ordifferent substituents, substituents which may be mentioned being:

straight-chain or branched alkyl or alkoxy each having 1 to 4 carbonatoms, cycloalkyl having 3 to 6 carbon atoms, the hydroxyl or the oxogroup, straight-chain or branched alkenyl having 2 to 4 carbon atoms,hydroxycarbonyl, alkoxycarbonyl having 1 to 4 carbon atoms in thestraight-chain or branched alkyl part, carbamoyl, alkylcarbamoyl ordialkylcarbamoyl each having 1 to 4 carbon atoms in the straight-chainor branched alkyl part, or phenyl or phenylalkyl which has 1 to 4 carbonatoms in the straight-chain or branched alkyl part and each of which isoptionally monosubstituted or disubstituted by identical or differentsubstituents from the series comprising halogen or straight-chain orbranched alkyl or alkoxy each having 1 to 4 carbon atoms; preferablystands for hydrogen or straight-chain or branched alkyl having 1 to 6carbon atoms, preferably stands for hydrogen, straight-chain or branchedalkyl having 1 to 6 carbon atoms, phenylalkyl which has 1 to 4 carbonatoms in the straight-chain or branched alkyl part and is optionallymonosubstituted to pentasubstituted by identical or differentsubstituents, phenyl substituents which may be mentioned being: halogen,alkyl or alkoxy each having 1 to 4 carbon atoms, or halogenoalkyl orhalogenoalkoxy each having 1 to 2 carbon atoms and 2 to 5 identical ordifferent halogen atoms; R^(II) furthermore stands foralkoxycarbonylalkyl, carbamoylalkyl, alkylcarbamoylalkyl ordialkylcarbamoylalkyl each having 1 to 4 carbon atoms in each alkylpart, or for cycloalkyl having 3 to 6 carbon atoms which is optionallysubstituted by straight-chain or branched alkyl having 1 to 4 carbonatoms,

preferably stands for hydrogen, straight-chain or branched alkyl having1 to 6 carbon atoms, phenylalkyl which has 1 to 4 carbon atoms in thestraight-chain or branched alkyl part and is optionally monosubstitutedto pentasubstituted by identical or different substituents, suitablephenyl substituents being the phenyl substituents mentioned as preferredin the case of R^(II) ; R^(III) furthermore stands foralkoxycarbonylalkyl, carbamoylalkyl, alkylcarbamoylalkyl ordialkylcarbamoylalkyl each having 1 to 4 carbon atoms in each alkylpart, or for cycloalkyl having 3 to 6 carbon atoms which is optionallysubstituted by straight-chain or branched alkyl having 1 to 4 carbonatoms;

R^(IV) preferably stands for hydrogen, straight-chain or branched alkylhaving 1 to 6 carbon atoms, phenylalkyl which has 1 to 4 carbon atoms inthe straight-chain or branched alkyl part and is optionallymonosubstituted to pentasubstituted by identical or differentsubstituents, suitable phenyl substituents preferably being the phenylsubstituents mentioned in the case of R^(II) ; or R^(IV) furthermorestands for acyl having 2 to 9 carbon atoms;

n preferably stands for the numbers 0, 1 or 2, and

X preferably stands for oxygen or sulphur.

Particularly preferred N,N'-diacylaminals are those of the generalformula (I) in which

R¹ stands for straight-chain or branched alkyl having 1 to 4 carbonatoms which is optionally monosubstituted, disubstituted ortrisubstituted by identical or different substituents, suitablesubstituents being the following: fluorine, chlorine, bromine, iodine,cyano, --COOR^(I), --CONR^(II) R^(III), --OR^(IV), acyl having 2 to 9carbon atoms, phenyl which is optionally monosubstituted, disubstitutedor trisubstituted by identical or different substituents from the seriescomprising fluorine, chlorine, methyl and methoxy, cyclopropyl orcyclohexyl, each of which is optionally monosubstituted, disubstitutedor trisubstituted by methyl, or heterocyclic rings of the formulae##STR6## which are optionally monosubstituted, disubstituted ortrisubstituted by identical or different alkyl having 1 or 2 carbonatoms;

R¹ furthermore stands for allkyl or propargyl, each of which isoptionally monosubstituted or disubstituted by methyl, or forcyclopropyl, cyclohexyl, cyclopentyl or cyclohexenyl, each of which isoptionally monosubstituted, disubstituted or trisubstituted by methyl;

R² stands for hydrogen or straight-chain or branched alkyl having 1 to 4carbon atoms which is optionally monosubstituted, disubstituted ortrisubstituted by identical or different substituents, suitablesubstituents being the following: cyano, methoxy, ethoxy, methylthio,ethylthio, --COOR^(I), acylamino having 2 to 9 carbon atoms, phenylwhich is optionally monosubstituted, disubstituted or trisubstituted byidentical or different substituents from the series comprising halogen,methyl and methoxy, cyclopropyl or cyclohexyl, each of which isoptionally monosubstituted, disubstituted or trisubstituted by methyl,or heterocyclic rings of the formulae ##STR7## each of which isoptionally monosubstituted, disubstituted or trisubstituted by identicalor different alkyl having 1 or 2 carbon atoms;

R² furthermore stands for allyl, allenyl, vinyl, propargyl or ethinyl,each of which is optionally substituted by phenyl which may optionallybe monosubstituted, disubstituted or trisubstituted by identical ordifferent substituents from the series comprising halogen and methyl;

R² in addition stands for cyclopropyl, cyclohexyl, cyclopentenyl orcyclohexenyl; R² additionally stands for phenyl which is optionallymonosubstituted, disubstituted or trisubstituted by identical ordifferent substitents from the series comprising halogen, methyl andmethoxy, or heterocyclic rings of the formulae ##STR8## each of which isoptionally monosubstituted, disubstituted or trisubstituted by identicalor different alkyl having 1 to 2 carbon atoms;

R³ stands for hydrogen or straight-chain or branched alkyl having 1 to 4carbon atoms which is optionally monosubstituted, disubstituted ortrisubstituted by identical or different substituents, suitablesubstituents being the following: fluorine, chlorine, bromine, iodine,cyano, alkoxy, alkylthio, alkylsulphinyl and alkylsulphonyl each having1 or 2 carbon atoms, acyloxy and acylamino each having 2 to 9 carbonatoms, --COOR^(I), cyclopropyl, cyclopentyl, cyclohexyl or phenyl whichis optionally monosubstituted, disubstituted or trisubstituted byidentical or different substituents from the series comprising halogenand methyl, or heterocyclic rings of the formulae ##STR9## each of whichis optionally monosubstituted, disubstituted or trisubstituted byidentical or different alkyl having 1 or 2 carbon atoms; R³ furthermorestands for vinyl or ethinyl, each of which is optionally substituted byphenyl which may optionally be monosubstituted, disubstituted ortrisubstituted by identical or different substituents from the seriescomprising halogen and methyl, or by methyl; R³ additionally stands forcyclopropyl, cyclopentyl, cyclohexyl, cyclopentenyl or cyclohexenyl,each of which is optionally bridged by methylene or ethylene and/orfused to 1 or 2 benzene, cyclopentane or cyclohexane rings and each ofwhich is optionally monosubstituted, disubstituted or trisubstituted byidentical or different substituents, substituents which may be mentionedbeing: halogen, methyl, methoxy, acyloxy and acylamino each having 2 to5 carbon atoms, the oxo group, phenyl, hydroxycarbonyl, methoxycarbonyland ethoxycarbonyl; R³ in addition stands for phenyl which is optionallyfused to 1 or 2 benzene or cyclohexane rings and is optionallymonosubstituted, disubstituted or trisubstituted by identical ordifferent substituents, substituents which may be mentioned being:fluorine, chlorine, hydroxyl, nitro, methyl, methoxy, acylamino andN-alkyl-acyl-amino each having 2 to 5 carbon atoms in the acyl part and1 or 2 carbon atoms in the alkyl part, hydroxycarbonyl, methoxycarbonyland ethoxycarbonyl; R³ furthermore stands for 5- or 6-memberedheterocyclyl having 1 to 3 identical or different hetero atoms, such asnitrogen, oxygen and sulphur atoms, which is optionally fused to 1 or 2benzene or cyclohexane rings and is optionally monosubstituted,disubstituted or trisubstituted by identical or different substituents,substituents which may be mentioned being: acyl having 2 to 5 carbonatoms, chlorine, bromine, methyl, ethyl, phenyl, oxo and hydroxyl;finally, R³ alternatively stands for alkoxycarbonyl having 1 to 4 carbonatoms in the alkoxy part, or for --OR⁴, --SR⁴ or --NR⁵ R⁶ ;

R⁴ stands for straight-chain or branched alkyl having 1 to 4 carbonatoms which is optionally monosubstituted, disubstituted ortrisubstituted by identical or different substituents, suitablesubstituents being the following: fluorine, chlorine, --OR^(IV),--SR^(IV), --COOR^(I), --CONR^(II) R^(III), CN, NR^(II) R^(III),alkylcarbonyl having 1 to 4 carbon atoms in the straight-chain orbranched alkyl part, phenyl or phenoxy, each of which is optionallymonosubstituted, disubstituted or trisubstituted by identical ordifferent substituents from the series comprising halogen and methyl,cyclopropyl, cyclohexyl, cyclopentenyl or cyclohexenyl, each of which isoptionally monosubstituted, disubstituted or trisubstituted by methyl,or 3- to 6-membered heterocyclyl having 1 to 3 identical or differenthetero atoms, such as nitrogen, oxygen and sulphur atoms, which isoptionally monosubstituted, disubstituted or trisubstituted by identicalor different substituents from the series comprising halogen, methyl andethyl; R⁴ furthermore stands for allyl or propargyl, each of which isoptionally monosubstituted or disubstituted by methyl, or forcyclopropyl, cyclohexyl, cyclopentenyl or cyclohexenyl, each of which isoptionally monosubstituted, disubstituted or trisubstituted by methyl;

R⁵ stands for hydrogen or for straight-chain or branched alkyl having 1to 4 carbon atoms which is optionally monosubstituted or disubstitutedby identical or different substituents, substituents which maypreferably be mentioned being: halogen, cyano, --COOR^(I), --CONR^(II)R^(III), NR^(II) R^(III) --OR^(IV), --S(O)_(n) R^(IV), acyl having 2 to9 carbon atoms, phenyl which is optionally monosubstituted,disubstituted or trisubstituted by identical or different substituentsfrom the series comprising halogen and alkyl having 1 to 4 carbon atoms,a 5- or 6-membered heterocyclic ring having 1 to 3 identical ordifferent hetero atoms, in particular nitrogen, oxygen and sulphur,which is optionally monosubstituted, disubstituted or trisubstituted byidentical or different substituents from the series comprising halogenand straight-chain or branched alkyl and alkoxy each having 1 to 4carbon atoms, or cycloalkyl having 3 to 6 carbon atoms or cycloalkenylhaving 5 to 7 carbon atoms, each of which is optionally substituted bystraight-chain or branched alkyl having 1 to 4 carbon atoms;

R⁵ furthermore particularly preferably stands for straight-chain orbranched alkenyl or alkinyl each having 2 to 6 carbon atoms, forcycloalkenyl having 5 to 7 carbon atoms which is optionally substitutedby straight-chain or branched alkyl having 1 to 4 carbon atoms, foroptionally substituted cycloalkyl having 3 to 6 carbon atoms,substituents which may preferably be mentioned being: halogen,straight-chain or branched alkyl and alkoxy each having 1 to 4 carbonatoms, cyano, amino, carbamoyl, in each case straight-chain or branchedalkylamino, dialkylamino, alkylcarbamoyl and dialkylcarbamoyl eachhaving 1 to 4 carbon atoms in each alkyl part, alkoxycarbonylaminohaving 1 to 4 carbon atoms in the straight-chain or branched alkoxypart, cycloalkyl and cycloalkylalkyl each having 5 or 6 carbon atoms inthe cycloalkyl part and 1 to 4 carbon atoms in the straight-chain orbranched alkyl part, or phenyl or pyrrolidone, each of which isoptionally monosubstituted, disubstituted or trisubstituted by identicalor different substituents from the series comprising halogen and alkylhaving 1 to 4 carbon atoms; R⁵ additionally particularly preferablystands for phenyl which is optionally monosubstituted, disubstituted ortrisubstituted by identical or different substituents from the seriescomprising halogen, straight-chain or branched alkyl or alkoxy eachhaving 1 to 4 carbon atoms, and halogenoalkyl or halogenoalkoxy eachhaving 1 or 2 carbon atoms and 1 to 5 identical or different halogenatoms, or for a 5- or 5-membered heterocyclic ring having 1 to 3identical or different hetero atoms, such as, in particular, nitrogen,oxygen or sulphur, which is optionally monosubstituted, disubstituted ortrisubstituted by identical or different substituents; substituentswhich may be mentioned for the heterocyclic rings are: halogen,mercapto, phenyl, straight-chain or branched alkyl, alkoxy, alkylthio,alkylsulphinyl and alkylsulphonyl having 1 to 4 carbon atoms per alkyl;

R⁶ stands for the meanings of R⁵ or the --OR^(IV) group, or

R⁵ and R⁶, together with the nitrogen atom to which they are bonded,stand for a monocyclic, bicyclic or tricyclic heterocyclic ring orspiroheterocyclic ring which is optionally monosubstituted topentasubstituted by identical or different substituents, heterocyclicrings which may be mentioned being: oxazolidine, pyrrolidine,imidazolidine, piperidine, piperazine, morpholine, thiomorpholine,1,3-oxazane or 1,3-diazane; each of these heterocyclic rings mayoptionally be fused to 1 or 2 benzene or cyclohexane rings or optionallybridged by methylene or ethylene. Substituents which may be mentionedfor all hetero systems are: straight-chain or branched alkyl orcycloalkyl having 3 to 6 carbon atoms, the hydroxyl or the oxo group,straight-chain or branched alkenyl having 2 to b 4 carbon atoms,hydroxycarbonyl, alkoxycarbonyl having 1 to 4 carbon atoms in thestraight-chain or branched alkyl part, carbamoyl, alkylcarbamoyl ordialkylcarbamoyl each having 1 to 4 carbon atoms in each alkyl part, andfurthermore phenyl or phenylalkyl which has 1 to 4 carbon atoms in thestraight-chain or branched alkyl part and each of which is optionallymonosubstituted or disubstituted by identical or different substituentsfrom the series comprising halogen and straight-chain or branched alkyland alkoxy each having 1 to 4 carbon atoms,

R^(I) stands for straight-chain or branched alkyl having 1 to 4 carbonatoms,

R^(II) stands for hydrogen, straight-chain or branched alkyl having 1 to4 carbon atoms, benzyl or phenethyl, each of which is optionallymonosubstituted, disubstituted or trisubstituted by identical ordifferent substituents, phenyl substituents which may be mentioned ineach case being: fluorine, chlorine, methyl, methoxy and trifluoromethy;R^(II) furthermore stands for alkoxycarbonyl having 1 to 4 carbon atomsin the alkoxy part and 1 or 2 carbon atoms in the alkyl part,carbamoylalkyl having 1 to 2 carbon atoms in the alkyl part,alkylcarbamoylalkyl or dialkylcarbamoylalkyl each having 1 or 2 carbonatoms in each alkyl part, or cycloalkyl having 3 to 6 carbon atoms whichis optionally monosubstituted, disubstituted or trisubstituted byidentical or different substituents from the series comprising methyland ethyl,

R^(III) stands for the meanings of R^(II),

R^(IV) stands for hydrogen, straight-chain or branched alkyl having 1 to4 carbon atoms, or benzyl or phenethyl, each of which is optionallymonosubstituted, disubstituted or trisubstituted by identical ordifferent substituents, phenyl substituents which may be mentioned ineach case being: fluorine, chlorine, methyl, methoxy andtrifluoromethyl; R^(IV) furthermore stands for acyl having 2 to 9 carbonatoms;

n stands for the numbers 0, 1 or 2, and

X stands for oxygen or sulphur.

Very particularly preferred N,N'-diacylaminals are those of the generalformula (I) in which

R¹ stands for alkyl having 1 to 2 carbon atoms which is optionallymonosubstituted or disubstituted by identical or different substituents,suitable substituents being the following: fluorine, chlorine, cyano,--COOR^(I), --CONR^(II) R^(III), --OR^(IV), alkylcarbonyl having 1 to 4carbon atoms in the straight-chain or branched alkyl part, phenyl whichis optionally monosubstituted, disubstituted or trisubstituted byidentical or different substituents from the series comprising fluorine,chlorine and methyl, cyclopropyl or cyclohexyl, each of which isoptionally monosubstituted, disubstituted or trisubstituted by methyl,and the following heterocyclic rings: ##STR10## R¹ furthermore standsfor allyl or propargyl, or for cyclopropyl, cyclohexyl, cyclopentenyl orcyclohexenyl, each of which is optionally monosubstituted, disubstitutedor trisubstituted by methyl;

R² stands for hydrogen or for alkyl having 1 to 4 carbon atoms which isoptionally monosubstituted or disubstituted by identical or differentsubstituents, suitable substituents being the following: cyano, methoxy,ethoxy, methylthio, ethylthio, --COOR^(I), alkylcarbonylamino having 1to 4 carbon atoms in the straight-chain or branched alkyl part, phenylwhich is optionally monosubstituted, disubstituted or trisubstituted byidentical or different substituents from the series comprising halogen,methyl and methoxy, cyclopropyl or cyclohexyl, each of which isoptionally monosubstituted, disubstituted or trisubstituted by methyl,and the following heterocyclic rings: ##STR11## R² furthermore standsfor vinyl, allyl, allenyl, ethinyl or propargyl, each of which isoptionally substituted by phenyl which may optionally bemonosubstituted, disubstituted or trisubstituted by identical ordifferent substituents from the series comprising halogen and methyl; R²in addition stands for cyclopropyl, cyclohexyl, cyclopentenyl orcyclohexenyl; R² additionally stands for phenyl which is optionallymonosubstituted, disubstituted or trisubstituted by identical ordifferent substituents from the series comprising halogen, methyl andmethoxy, or for the following heterocyclic rings: ##STR12## R³ standsfor hydrogen or for straight-chain or branched alkyl having 1 to 4carbon atoms which is optionally monosubstituted or disubstituted byidentical or different substituents, suitable substituents being thefollowing: fluorine, chlorine, bromine, iodine, cyano, alkoxy,alkylthio, alkylsulphinyl and alkylsulphonyl each having 1 to 2 carbonatoms, alkylcarbonyloxy having 1 to 4 carbon atoms in the straight-chainor branched alkyl part, formamido, alkylcarbonylamino having 1 or 2carbon atoms in the alkyl part, which is optionally substituted byfluorine, benzoylamino which is optionally substituted by chlorine,alkoxycarbonylamino having 1 to 4 carbon atoms in the straight-chain orbranched alkoxy part, --COOR^(I), cyclopropyl, cyclopentyl, cyclohexylor phenyl which is optionally monosubstituted, disubstituted ortrisubstituted by identical or different substituents from the seriescomprising halogen and methyl, and the following heterocyclic rings:##STR13## R³ furthermore stands for vinyl or ethinyl, each of which isoptionally monosubstituted or disubstituted by identical or differentsubstituents from the series comprising phenyl which may optionally bemonosubstituted, disubstituted or trisubstituted by identical ordifferent substituents from the series comprising halogen and methyl, orby methyl; R³ additionally stands for cyclopropyl, cyclopentyl,cyclohexyl, cyclopentenyl or cyclohexenyl, each of which is optionallybridged by methylene or ethylene and/or fused to 1 or 2 benzene,cyclopentane or cyclohexane rings and each of which is optionallymonosubstituted, disubstituted or trisubstituted by identical ordifferent substituents, substitutents which may be mentioned being:halogen, methyl, the oxo group, phenyl, hydroxycarbonyl, methoxycarbonyland ethoxycarbony; the following rings may be mentioned individually:##STR14## R³ in addition stands for phenyl which is optionally fused to1 or 2 benzene, cyclopentane or cyclohexane rings and is optionallymonosubstituted, disubstituted or trisubstituted by identical ordifferent substituents, substituents which may be mentioned being:fluorine, chlorine, hydroxyl, nitro, methyl, methoxy, acetoxy,acetamido, hydroxycarbonyl, methoxycarbonyl and ethoxycarbonyl; R³furthermore stands for 5- or 6-membered heterocyclyl having 1 to 3identical or different hetero atoms, such as nitrogen, oxygen andsulphur atoms, which is optionally fused to 1 or 2 benzene orcyclohexane rings and is optionally monosubstituted, disubstituted ortrisubstituted by identical or different substituents, substituentswhich may be mentioned being: acyl having 2 to 5 carbon atoms, chlorine,bromine, methyl, ethyl, phenyl, the oxo group and hydroxyl; thefollowing heterocyclic rings may be mentioned individually: ##STR15##Finally, R³ alternatively stands for alkoxycarbonyl having 1 to 4 carbonatoms in the straight-chain or branched alkoxy part, or for --OR⁴, --SR⁴or --NR⁵ R⁶ ;

R⁴ stands for straight-chain or branched alkyl having 1 or 2 carbonatoms which is optionally monosubstituted or disubstituted by identicalor different substituents, suitable substituents being the following:fluorine, chlorine, methoxy, ethoxy, methylthio, alkoxycarbonyl having 1to 4 carbon atoms in the straight-chain or branched alkyl part,carbamoyl, methylcarbamoyl, dimethylcarbamoyl, cyano, dimethylamino,diethylamino, acetyl, pivaloyl, or phenyl or phenoxy, each of which isoptionally monosubstituted, disubstituted or trisubstituted by identicalor different substituents from the series comprising halogen and methyl,and cyclopropyl or cyclohexyl, each of which is optionallymonosubstituted, disubstituted or trisubstituted by methyl; R⁴furthermore stands for 3- to 6-membered heterocyclyl having 1 to 3identical or different hetero atoms, such as nitrogen, oxygen andsulphur atoms, which is optionally monosubstituted, disubstituted ortrisubstituted by identical or different substituents from the seriescomprising halogen, methyl and ethyl; the following heterocyclic ringsmay be mentioned individually: ##STR16## R⁴ in addition stands for allylor propargyl, each of which is optionally monosubstituted ordisubstituted by methyl, or for cyclohexyl which is optionallymonosubstituted, disubstituted or trisubstituted by methyl;

R⁵ stands for hydrogen, straight-chain or branched alkyl having 1 to 4carbon atoms, or alkyl having 1 to 3 carbon atoms which ismonosubstituted or disubstituted by identical or different substituents,suitable substituents being: chlorine, hydroxyl, alkylcarbonyloxy having1 to 4 carbon atoms in the straight-chain or branched alkyl part,alkylcarbonyl having 1 to 4 carbon atoms in the straight-chain orbranched alkyl part, alkoxy and alkylthio each having 1 or 2 carbonatoms, alkoxycarbonyl having 1 to 4 carbon atoms in the straight-chainor branched alkoxy part, carbamoyl, methylcarbamoyl, dimethylcarbamoyl,cyano, dimethylamino, diethylamino, 2-furyl, 2-pyridyl, 1-morpholino,cyclopropyl, cyclohexyl or phenyl which is optionally monosubstituted,disubstituted or trisubstituted by identical or different substituentsfrom the series comprising chlorine and methyl; R⁵ furthermore veryparticularly preferably stands for allyl or propargyl, for1-cyclohexenyl, or for cyclohexyl which is monosubstituted,disubstituted or trisubstituted by identical or different substituents,suitable substituents being: chlorine, methyl, ethyl, methoxy, cyano,amino, alkylamino and dialkylamino each having 1 or 2 carbon atoms ineach alkyl part, carbamoyl, alkylcarbamoyl and dialkylcarbamoyl eachhaving 1 or 2 carbon atoms in each alkyl part, cyclohexyl,cyclohexylalkyl having 1 or 2 carbon atoms in the alkyl part, or1-pyrrolidin-2-one; R⁵ in addition very particularly preferably standsfor phenyl which is optionally monosubstituted, disubstituted ortrisubstituted by identical or different substituents from the seriescomprising chlorine and methyl, for 2-pyridyl or 2-pyrimidinyl, each ofwhich is optionally monosubstituted, disubstituted or trisubstituted bymethyl, for 2-thiazolyl which is optionally substituted by phenyl, for2-benzothiazolyl which is optionally monosubstituted, disubstituted ortrisubstituted by identical or different substituents from the seriescomprising chlorine, methyl and methoxy, for 1,2,4-triazol-3-yl, for1,2,4-thiadiazol-5-yl which is optionally substituted by phenyl, for1,3,4-thiadiazol-5-yl which is optionally monosubstituted, disubstitutedor trisubstituted by identical or different substituents from the seriescomprising mercapto, straight-chain or branched alkyl having 1 to 4carbon atoms, and in each case straight-chain or branched alkylthio,alkylsulphinyl and alkylsulphonyl each having 1 to 4 carbon atoms, orfor the ##STR17## group, R⁶ stands for hydrogen, straight-chain orbranched alkyl having 1 to 4 carbon atoms, or alkyl having 1 to 3 carbonatoms which is monosubstituted or disubstituted by identical ordifferent substituents, substituents which may be mentioned being:chlorine, hydroxyl, alkylcarbonyloxy having 1 to 4 carbon atoms in thestraight-chain or branched alkyl part, alkylcarbonyl having 1 to 4carbon atoms in the straight-chain or branched alkyl part, alkoxy andalkylthio each having 1 or 2 carbon atoms, alkoxycarbonyl having 1 to 4carbon atoms in the straight-chain or branched alkoxy part, carbamoyl,methylcarbamoyl, dimethylcarbamoyl, cyano, dimethylamino, diethylamino,or 2-furyl, 2-pyridyl, 1-morpholino, cyclopropyl, cyclohexyl or phenylwhich is optionally monosubstituted, disubstituted or trisubstituted byidentical or different substituents from the series comprising chlorineand methyl; R⁶ furthermore very particularly preferably stands for allylor propargyl, for 1-cyclohexenyl, or for cyclohexyl which ismonosubstituted, disubstituted or trisubstituted by identical ordifferent substituents, substituents which may be mentioned being:chlorine, methyl, ethyl, methoxy, cyano, amino, alkylamino ordialkylamino each having 1 or 2 carbon atoms in each alkyl part,carbamoyl, alkylcarbamoyl or dialkylcarbamoyl each having 1 or 2 carbonatoms in each alkyl part, cyclohexyl, cyclohexylalkyl having 1 or 2carbon atoms in the alkyl part, or 1-pyrrolidin-2-one; R⁶ in additionvery particularly preferably stands for phenyl which is optionallymonosubstituted, disubstituted or trisubstituted by identical ordifferent substituents from the series comprising chlorine and methyl,for 2-pyridyl or 2-pyrimidyl, each of which is optionallymonosubstituted, disubstituted or trisubstituted by methyl, for2-thiazolyl which is optionally substituted by phenyl, for2-benzothiazolyl which is optionally monosubstituted, disubstituted ortrisubstituted by identical or different substituents from the seriescomprising chlorine, methyl and methoxy, for 1,2,4 -triazol-3-yl, for1,2,4-thiadiazol-5-yl which is optionally substituted by phenyl, for1,3,4-thiadiazol-5-yl which is optionally monosubstituted, disubstitutedor trisubstituted by identical or different substituents from the seriescomprising mercapto, straight-chain or branched alkyl having 1 to 4carbon atoms, and in each case straight-chain or branched alkylthio,alkylsulphinyl and alkylsulphonyl each having 1 to 4 carbon atoms, orfor the ##STR18## group, R⁶ additionally very particularly preferablystands for hydroxyl, alkoxy having 1 or 2 carbon atoms, for benzyloxywhich is optionally monosubstituted, disubstituted or trisubstituted byidentical or different substituents from the series comprising chlorineand methyl, for 1-adamantyl, 2-norbornyl, 1- or 2-decalyl or 1- or2-tertralyl; or

R⁵ and R⁶, together with the nitrogen atom to which they are bonded,stand for the following monocyclic, bicyclic or tricyclic heterocyclicrings or spiroheterocyclic rings: ##STR19## where Z¹ stands forhydroxyl, methoxy, ethoxy, amino, methylamino, ethylamino, dimethylaminoor methylethylamino,

Z² stands for oxygen or the CH₂ group,

m stands for the numbers 0, 1, 2, 3 or 4,

p stands for the numbers 0, 1 or 2,

q stands for the numbers 0, 1, 2 or 3,

R^(I) stands for methyl, ethyl, n- or i-propyl and n-, i-, s- ort-butyl,

R^(II) and R^(III) are identical or different and stand for hydrogen,methyl, ethyl, n- or i-propyl, for benzyl which is optionallymonosubstituted, disubstituted or trisubstituted by identical ordifferent substituents, with chlorine and methyl as substituents, foralkoxycarbonylalkyl having 1 or 2 carbon atoms in each alkyl part, forcarbamoylalkyl, alkylcarbamoylalkyl or dialkylcarbamoylalkyl each having1 or 2 carbon atoms in each alkyl part, or for cyclohexyl which isoptionally monosubstituted, disubstituted or trisubstituted by methyl,

R^(IV) stands for hydrogen, alkyl having 1 or 2 carbon atoms, for benzylwhich is optionally monosubstituted, disubstituted or trisubstituted byidentical or different substituents, phenyl substituents which may bementioned being fluorine, chlorine and methyl; and

X stands for oxygen or sulphur.

Apart from the compounds mentioned in the preparation examples, thesubstances of the formula (I) listed in the table below may be mentionedas examples of compounds according to the invention:

    __________________________________________________________________________     ##STR20##                           (I)                                      R.sup.1   R.sup.2   R.sup.3          X                                        __________________________________________________________________________    CH.sub.3  H         H                O                                        CH.sub.3  H         CH.sub.2OCH.sub.3                                                                              O                                        CH.sub.3  H         CHCl.sub.2       O                                        CH.sub.3  H                                                                                        ##STR21##       O                                        CH.sub.3  H                                                                                        ##STR22##       O                                        CH.sub.3  H                                                                                        ##STR23##       O                                        CH.sub.3  H                                                                                        ##STR24##       O                                        CH.sub.3  H                                                                                        ##STR25##       O                                        CH.sub.3  H                                                                                        ##STR26##       O                                        CH.sub.3  H                                                                                        ##STR27##       O                                        CH.sub.3  H                                                                                        ##STR28##       O                                        CH.sub.3  H         OCH(CH.sub.3).sub.2                                                                            O                                        CH.sub.3  H                                                                                        ##STR29##       O                                        CH.sub.3  H                                                                                        ##STR30##       O                                        CH.sub.3  H         N(C.sub.2 H.sub.5).sub.2                                                                       O                                        CH.sub.3  H                                                                                        ##STR31##       O                                        CH.sub.3  H         SC.sub.2 H.sub.5 O                                        CH.sub.3  H         NHCH.sub.3       S                                        CH.sub.3  H                                                                                        ##STR32##       O                                        CH.sub.3  CH.sub.3  CH.sub.3         O                                        CH.sub.3                                                                                 ##STR33##                                                                              CH.sub.3         O                                        CH.sub.2CN                                                                              H         CH.sub.3         O                                         ##STR34##                                                                              H         CH.sub.3         O                                        CH.sub.3  H         COOC.sub.2 H.sub.5                                                                             O                                        CH.sub.3  H         OCH.sub.2CCl.sub.3                                                                             O                                        CH.sub.3  H         OCH.sub.2 CH.sub.2OCH.sub.3                                                                    O                                        CH.sub.3  H                                                                                        ##STR35##       O                                        CH.sub.3  H         OCH.sub.2 CH.sub.2 CN                                                                          O                                        CH.sub.3  H         OCH.sub.2CONH.sub.2                                                                            O                                        CH.sub.3  H         OCH.sub.2 CH.sub.2N(CH.sub.3).sub.2                                                            O                                        CH.sub.3  H                                                                                        ##STR36##       O                                        CH.sub.3  H                                                                                        ##STR37##       O                                        CH.sub.3  H                                                                                        ##STR38##       O                                        CH.sub.3  H                                                                                        ##STR39##       O                                        CH.sub.3  H                                                                                        ##STR40##       O                                        CH.sub.3  H         OCH.sub.2CHCH.sub.2                                                                            O                                        CH.sub.3  H         OCH.sub.2CCH     O                                        CH.sub.3  H                                                                                        ##STR41##       O                                        CH.sub.3  H         CH.sub.2SCH.sub. 3                                                                             O                                        CH.sub.3  H         CH.sub.2SO.sub.2CH.sub.3                                                                       O                                        CH.sub.3  H         CHCH.sub.2       O                                        CH.sub.3  H         CH.sub.2CN       O                                        CH.sub.3  H         CH.sub.2OCOCH.sub.3                                                                            O                                        CH.sub.3  H         CH.sub.2NHCOCH.sub.3                                                                           O                                        CH.sub.3  H         CH.sub.2COOCH.sub.3                                                                            O                                        CH.sub.3  H                                                                                        ##STR42##       O                                        CH.sub.3  H                                                                                        ##STR43##       O                                        CH.sub.3  H                                                                                        ##STR44##       O                                        CH.sub.3  H                                                                                        ##STR45##       O                                        CH.sub.3  H                                                                                        ##STR46##       O                                        CH.sub.3  H                                                                                        ##STR47##       O                                        CH.sub.3  H                                                                                        ##STR48##       O                                        CH.sub.3  H                                                                                        ##STR49##       O                                        CH.sub.3  H         NH.sub.2         O                                        CH.sub.3  H                                                                                        ##STR50##       O                                        CH.sub.3  H         NHCH.sub.2COOC.sub.2 H.sub.5                                                                   O                                        CH.sub.3  H         NHCH.sub.2CN     O                                        CH.sub.3  H                                                                                        ##STR51##       O                                        CH.sub.3  H                                                                                        ##STR52##       O                                        CH.sub.3  H         NHCH.sub.2CHCH.sub.2                                                                           O                                        CH.sub.3  H         NHCH.sub.2CCH    O                                        CH.sub.3  H         NHCH.sub.2CON(C.sub.2 H.sub.5).sub.2                                                           O                                        CH.sub.3  H         N(CH.sub.3).sub.2                                                                              S                                        CH.sub.3  H         OC.sub.2 H.sub.5 S                                        __________________________________________________________________________

If, for example, N-aminomethyl-(E)-2-cyano-2-methoximinoacetamidehydrochloride is used as starting material, acetyl chloride as acylatingreagent and triethylamine as base and 4-dimethylaminopyridine ascatalyst, the course of process (a) according to the invention may berepresented by the following equation: ##STR53##

If, for example, (E)-2-cyano-2-methoximinoacetaminomethyl isocyanate andmethylamine are used as starting materials, the course of the process(b) according to the invention may be represented by the followingequation: ##STR54##

Formula (II) provides a general definition of the2-cyano-2-oximino-acetamides to be used as starting materials forcarrying out process (a) according to the invention. In this formula, R¹and R² have the meanings which have already been mentioned for thesesubstituents in connection with the description of the substances offormula (I) according to the invention, including the preferred,particularly preferred and very particularly preferred meaningshereinabove. HY preferably stands for the equivalent of a mineral acid,such as, for example, hydrochloric acid, or of a carboxylic acid, suchas, for example, oxalic acid.

The 2-cyano-2-oximino-acetamides of the formula (II) were hithertounknown. However, they can be prepared in a known fashion by hydrolyzingisocyanates of the formula (IV) ##STR55## in which R¹ and R² have theabovementioned meaning,

in a customary fashion, and isolating the resultant amine as a salt in acustomary fashion.

The hydrolysis of the isocyanates of the formula (IV) is carried out inthe presence of a diluent. The following are preferably suitable in thiscase: water; nitriles, such as acetonitrile; ethers, such astetrahydrofuran, dioxane or dimethyl ether, or ketones, such as acetone.

The reaction temperatures may be varied within a relatively wide rangein the hydrolysis of the isocyanates of the formula (IV). In general,the hydrolysis is carried out at between -20° C. and 150° C., preferablybetween 20° C. and 80° C.

When carrying out the hydrolysis of the isocyanates of the formula (IV),the latter are preferably reacted in situ (for the preparation, see thedescription of process (b) according to the invention) with excesswater. The resultant amine is isolated as a salt by adding the acid, forexample hydrochloric acid, and subsequently carrying out the customarywork-up.

Formulae (IIIa) and (IIIb) provide general definitions of the acylatingreagents additionally to be used as starting materials for carrying outprocess (a) according to the invention. In the formula (IIIa), Xpreferably stands for oxygen or sulphur and Z preferably stands for aleaving group. These preferably include chlorine, bromine, alkoxy andalkylthio each having 1 to 4 carbon atoms, carboxymethoxy,carboxymethylthio and the --O--CO--R³, --O--CO--OR⁴ and SR⁴ groups. R³and R⁴ here preferably have the meanings which have already preferablybeen mentioned for these substituents in connection with the descriptionof the substances of the formula (I) according to the invention. In theformula (IIIb), X and R⁶ preferably have the meanings which have alreadypreferably been mentioned for these substituents in connection with thedescription of the substances of the formula (I) according to theinvention.

The acylating reagents of the formulae (IIIa) and (IIIb), i.e. carbonylhalides, carboxylic anhydrides, halogenoformates andhalogenothioformates, trithiocarbonates, pyrocarbonates, carbamoylhalides, carbamates, thiocarbamates, dithiocarbamates, isocyanates orisothiocyanates, are generally known compounds of organic chemistry orcan be obtained by generally customary methods.

Formula (IV) provides a general definition of the isocyanates to be usedas starting materials for carrying out process (b) according to theinvention and as precursors for process (a) according to the invention.In this formula, R¹ and R² have the meanings which have already beenmentioned for these substituents in connection with the description ofthe substances of the formula (I) according to the invention, includingthe preferred, particularly preferred and very particularly preferredmeanings hereinabove.

The isocyanates of the formula (IV) were hitherto unknown. However, theycan be prepared in a known fashion, for example by

(α) oxidizing amides of the general formula (VI) ##STR56## in which R¹and R² have the abovementioned meaning, in a customary fashion, ifappropriate in the presence of a diluent ("Hofmann degradation"), itbeing possible to further react the resultant isocyanates of the formula(IV) directly, if desired also without isolation; or

(β) warming azides of the general formula (VII) ##STR57## in which R¹and R² have the abovementioned meaning, in the presence of a diluent("Curtius degradation"), it being possible to further react theresultant isocyanates of the formula (IV) directly, if desired alsowithout isolation.

Oxidants which may preferably be mentioned for process variant (α) are:sodium hypochlorite, sodium hypobromite, lead tetraacetate andI,I-bis(trifluoroacetoxy)-iodobenzene [ ##STR58## I(OCOCF₃)₂ =J. Chem.Soc. Chem. Com. 1982, p. 280].

Suitable diluents for process variant (α) are inert organic solvents,such as, for example, ethers, such as tetrahydrofuran, dioxane ordimethyl ether, or nitriles, such as acetonitrile. In the case of directfurther reaction of the isocyanates of the formula (IV), suitablediluents are also water or alcohols, or mixtures thereof with inertorganic solvents, such as, for example, water/acetonitrile.

The reaction temperatures may be varied within a relatively wide rangein the oxidation in accordance with process variant (α). In general, theoxidation is carried out between -20° C. and 120° C., preferably between0° C. and 40° C.

When carrying out the oxidation in accordance with process variant (α),a slight excess of oxidant is preferably used, the isocyanates of theformula (IV) generally being further reacted directly without isolation.

Suitable diluents for process variant (β) are inert organic solvents,such as, for example, aromatic hydrocarbons, such as toluene orchlorobenzene; ethers, such as dioxane, or halogenated hydrocarbons,such as chloroform or methylene chloride. In the case of direct furtherreaction of the isocyanates of the formula (IV), suitable diluents arealso water or alcohols, or mixtures thereof with inert organic solvents.

The reaction temperatures may be varied within a relatively wide rangewhen carrying out process variant (β). In general, the process iscarried out between 0° C. and 150° C., preferably between 60° C. and100° C.

When carrying out process variant (β), the resultant isocyanates of theformula (IV) are generally further reacted directly without isolation.

The amides of the formula (VI) and the azides of the formula (VII) areknown (in this respect, compare, for example, EP-OS (European PublishedSpecification) 0,206,004 and DE-OS (German Published Specification)3,602,243), or can be obtained by the processes described therein.

Formulae (Va) and (Vb) provide general definitions of the proticnucleophiles additionally to be used as starting materials for carryingout process (b) according to the invention. In the formula (Va), R³preferably stands for the meanings which have already preferably beenmentioned for these substituents in connection with the description ofthe substances of the formula (I) according to the invention. In theformula (Vb), R⁷ preferably stands for the --OR⁴, --SR⁴ or --NR⁵ R⁶groups. R⁴, R⁵ and R⁶ here preferably have the meanings which havealready preferably been mentioned for these substituents in connectionwith the description of the substances of the formula (I) according tothe invention.

The protic nucleophiles of the formulae (Va) and (Vb), i.e. carboxylicacids, alcohols, thiols and amines, are generally known compounds oforganic chemistry or can be obtained by generally customary methods.

Suitable diluents for process (a) according to the invention are inertorganic solvents. These preferably include aromatic hydrocarbons, suchas toluene; halogenated hydrocarbons, such as methylene chloride orchloroform; ethers, such as tetrahydrofuran or 1,2-dimethoxyethane;esters, such as ethyl acetate; nitriles, such as acetonitrile; ketones,such as acetone; tertiary amines, such as pyridine; amines, such asdimethylformamide, or alternatively an appropriate excess of theacylating reagent of the formulae (IIIa) and (IIIb).

Process (a) is carried out in the presence of a base. In this case,suitable bases are customary organic and inorganic bases. Tertiaryamines, such as triethylamine or pyridine; alkoxides, such as sodiummethoxide, and alkali metal carbonates, such as potassium carbonate, maybe mentioned preferentially.

Process (a) according to the invention is carried out, if necessary, inthe presence of a catalyst. Examples mentioned are the tertiary amines,such as 4-dimethylaminopyridine, 1,8-diazabicyclo[5,4,0]undec-7-ene(DBU) or 1,4-diazabicyclo[2,2,2]-octane (DABCO); furthermore imidazoleand dimethylformamide.

The reaction temperatures may be varied within a relatively wide rangewhen carrying out process (a) according to the invention. In general,the process is carried out between -20° C. and 120° C., preferablybetween 0° C. and 40° C.

When carrying out process (a) according to the invention, equimolaramounts are preferably used, but it is also possible to employ the2-cyano-2-oximinoacetamides of the formula (II) of the acylatingreagents of the formula (IIIa) and (IIIb) in excess. The reaction iscarried out, and the reaction products of the formula (I) are worked upand isolated in a generally customary fashion.

Suitable diluents for process (b) according to the invention are inertorganic solvents. These preferably include aromatic hydrocarbons, suchas toluene; halogenated hydrocarbons, such as methylene chloride;ethers, such as tetrahydrofuran or dimethoxyethane; esters, such asethyl acetate; nitriles, such as acetonitrile, or alternatively anappropriate excess of a protic nucleophile of the formulae (Va) and(Vb).

Process (b) according to the invention is carried out, if necessary, inthe presence of a catalyst. Examples which may be mentioned are thecatalysts mentioned above in the case of process (a).

The reaction temperatures may be varied within a relatively wide rangewhen carrying out process (b) according to the invention. In general,the process is carried out between -20° C. and 150° C., preferablybetween 20° C. and 80° C.

When carrying out process (b) according to the invention, the isocyanateof the formula (IV) is preferably reacted in situ with an excess of anucleophile of the formulae (Va) or (Vb), the latter simultaneouslybeing used as a solvent. However, it is also possible to react theisolated isocyanates of the formula (IV) in equimolar amounts with thenucleophiles of the formulae (Va) and (Vb). The reaction is carried outand the reaction products of the formula (I) are worked up and isolatedin a generally customary fashion.

The active compounds according to the invention have a strongmicrobicidal action and can be employed in practice for combatingundesired microorganisms. The active compounds are suitable for use aspesticides.

For example fungicidal agents in plant protection are employed forcombating Plasmodiophoromycetes, Oomycetes, Chytridiomycetes,Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.

Some causative organisms of fungal and bacterial diseases which comeunder the generic names listed above may be mentioned as examples, butnot by way of limitation: Pythium species, such as, for example, Pythiumultimum; Phytophthora species, such as, for example, Phytophthorainfestans; Pseudoperonospora species, such as, for example,Pseudoperonospora humuli or Pseudoperonospora cubensis; Plasmoparaspecies, such as, for example, Plasmopara viticola; Peronospora species,such as, for example, Peronospora pisi or P. brassicae; Erysiphespecies, such as, for example, Erysiphe graminis; Sphaerotheca species,such as, for example, Sphaerotheca fuliginea; Podosphaera species, suchas, for example, Podosphaera leucotricha; Venturia species, such as, forexample, Venturia inaequalis; Pyrenophora species, such as, for example,Pyrenophora teres or P. graminea (conidia form: Drechslera, syn:Helminthosporium); Cochliobolus species, such as, for example,Cochliobolus sativus (conidia form: Drechslera, syn: Helminthosporium);Uromyces species, such as, for example, Uromyces appendiculatus;Puccinia species, such as, for example, Puccinia recondita; Tilletiaspecies, such as, for example, Tilletia caries; Ustilago species, suchas, for example, Ustilago nuda or Ustilago avenae; Pellicularia species,such as, for example, Pellicularia sasakii; Pyricularia species, suchas, for example, Pyricularia oryzae; Fusarium species, such as, forexample, Fusarium culmorum; Botrytis species, such as, for example,Botrytis cinerea; Septoria species, such as, for example, Septorianodorum; Leptosphaeria species, such as, for example, Leptosphaerianodorum; Cercospora species, such as, for example, Cercospora canescensand Pseudocercosporella species, such as, for example,Pseudocercosporella herpotrichoides.

The good toleration, by plants, of the active compounds, at theconcentrations required for combating plant diseases, permits treatmentof above-ground parts of plants, of vegetative propagation stock andseeds, and of the soil.

In pesticides, the active compounds according to the invention can beemployed particularly successfully for combating Phytophthora species,such as, for example, Phytophthora infestans, in tomatoes; and also forcombating Plasmopara species, such as, for example, Plasmopara viticola,in vines.

The active compounds can be converted to the customary formulations,such as solutions, emulsions, suspensions, powders, foams, pastes,granules, aerosols, natural and synthetic materials impregnated withactive compound, very fine capsules in polymeric substances and incoating compositions for seed, as well as ULV cold mist and warm mistformulations.

These formulations are produced in known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents, liquefiedgases under pressure, and/or solid carriers, optionally with the use ofsurface-active agents, that is, emulsifying agents and/or dispersingagents, and/or foam-forming agents. In the case of the use of water asan extender, organic solvents can, for example, also be used asauxiliary solvents. As liquid solvents, there are suitable in the main:aromatics, such as xylene, toluene or alkyl naphthalenes, chlorinatedaromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes,chloroethylenes or methylene chloride, aliphatic hydrocarbons, such ascyclohexane or paraffins, for example mineral oil fractions, alcohols,such as butanol or glycol as well as their ethers and esters, ketones,such as acetone, methyl ethyl ketone, methyl isobutyl ketone orcyclohexanone, strongly polar solvents, such as dimethylformamide anddimethylsulfoxide, as well as water; by liquefied gaseous extenders orcarriers are meant liquids which are gaseous at normal temperature andunder normal pressure, for example aerosol propellants, such ashalogenated hydrocarbons as well as butane, propane, nitrogen and carbondioxide; as solid carriers there are suitable: for example groundnatural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as highly disperse silicic acid, alumina and silicates;as solid carriers for granules there are suitable: for example crushedand fractionated natural rocks such as calcite, marble, pumice,sepiolite and dolomite, as well as synthetic granules of inorganic andorganic meals, and granules of organic material such as sawdust, coconutshells, corn cobs and tobacco stalks; as emulsifying and/or foam-formingagents there are suitable: for example non-ionic and anionicemulsifiers, such as polyoxyethylene-fatty acid esters,polyoxyethylene-fatty alcohol ethers, for example alkylaryl polyglycolethers, alkyl sulphonates, alkyl sulphates, aryl sulphonates as well asalbumin hydrolysis products; as dispersing agents there are suitable:for example lignin-sulphite waste liquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Further additives can bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations in general contain between 0.1 and 95% by weight ofactive compound, preferably between 0.5 and 90%.

The active compounds according to the invention can be present in theformulations or in the various use forms as a mixture with other knownactive compounds, such as fungicides, bactericides, insecticides,acaricides, nematicides, herbicides, bird repellents, growth factors,plant nutrients and agents for improving soil structure.

The active compounds can be used as such or in the form of theirformulations or the use forms prepared therefrom by further dilution,such as ready-to-use solutions, emulsions, suspensions, powders, pastesand granules. They are used in the customary manner, for example bywatering, immersion, spraying, atomizing, misting, vaporizing,injecting, forming a slurry, brushing on, dusting, scattering, drydressing, moist dressing, wet dressing, slurry dressing or encrusting.

In the treatment of parts of plants, the active compound concentrationsin the use forms can be varied within a relatively wide range. They are,in general, between 1 and 0.0001% by weight, preferably between 0.5 and0.001%.

In the treatment of seed, amounts of active compound of 0.001 to 50 gper kilogram of seed, preferably 0.01 to 10 g, are generally required.

For the treatment of soil, active compound concentrations of 0.00001 to0.1% by weight, preferably 0.0001 to 0.02% by weight, are required atthe place of action.

Preparation examples EXAMPLE 1 ##STR59## (Process a)

7.7 g (0.04 mol) of N-aminomethyl-(E)-2-cyano-2-methoximino-acetamidehydrochloride are suspended in 150 ml of methylene chloride, and 3.2 g(0.04 mol) of acetyl chloride and subsequently a solution of 8.08 g oftriethylamine and 0.49 g (0.004 mol) of 4-dimethylaminopyridine in 40 mlof methylene chloride are added dropwise at 0° C. The mixture is stirredfor 1 hour at 0° C. and for 18 hours at room temperature, washed twiceeach with 1 molar citric acid, 10 percent strength sodium bicarbonatesolution and saturated sodium chloride solution, dried over sodiumsulphate and evaporated in vacuo.

3.7 g are obtained as the first crude fraction.

The combined washings are extracted by shaking 5 times with methylenechloride, and the combined extracts are dried over sodium sulphate andevaporated. The residue (2.8 g) is recrystallized fromisopropanol/petroleum ether together with the 1st fraction. 4.96 g (62%of theory) of N-acetamidomethyl-(E)-2-cyano-2-methoximinoacetamide ofmelting point 162°-163° C. are obtained.

Preparation of the starting material ##STR60##

31 g (0.07 mol) of I,I-bis-(trifluoroacetoxy)iodobenzene (98% purity)are added to a solution of 12.4 g (0.067 mol) of N.sup.α-[(E)-2-cyano-2-methoximinoacetyl]-glycinamide in 150 ml ofacetonitrile/water (1:1), and the mixture is stirred at room temperaturefor 5 hours while nitrogen is passed through. The mixture is evaporatedin vacuo, the oily residue is dried by evaporating twice with ethylacetate and dissolved in 70 ml of ethyl acetate, and 10 ml of a 25percent strength ethereal hydrogen chloride solution are added. Theprecipitate is triturated in a mortar with ether and recrystallized fromacetonitrile/ether.

9.8 g (76% of theory) ofN-aminomethyl-(E)-2-cyano-2-methoximinoacetamide hydrochloride ofmelting point 122°-124° C. (decomposition) are obtained. ##STR61##

Ammonia is passed into a solution of 56.6 g (0.252 mol) ofN-[(E)-2-cyano-2-methoximinoacetyl]-glycine ethyl ester (95 percentpurity) in 300 ml of isopropanol at 0° to 10° C. until saturation isachieved, and the mixture is left to stand at room temperature for 4days. During this time, ammonia is passed in a further twice. Aftercooling to 0° C., the precipitate is filtered off under suction, washedwith cold isopropanol and dried at room temperature.

32 g (69% of theory) of N.sup.α-[(E)-2-cyano-2-methoximinoacetyl]-glycinamide of melting point170°-172° C. are obtained. ##STR62##

60.5 g (0.427 mol) of glycine ethyl ester hydrochloride are suspended in450 ml of dichloromethane, 86.2 g (0.853 mol) of triethylamine and 5.2 g(0.043 mol) of 4-dimethylaminopyridine are added, the reaction mixtureis stirred at 20° C. for 15 minutes, and a solution of 62.5 g (0.427mol) of 2-cyano-2-methyl-oximino-acetyl chloride (E isomer) is addeddropwise at 0° C. over one hour. The reaction mixture is subsequentlystirred for one hour at 0° C. and then for 5 hours at room temperature,and the solution is allowed to stand at room temperature for 2 days.After washing with 1M hydrochloric acid (twice with 300 ml in eachcase), saturated sodium bicarbonate solution (twice with 200 ml in eachcase) and water (twice with 300 ml in each case), the solution is driedover sodium sulphate and evaporated in vacuo.

81.0 g (89% of theory) of N-(2-cyano-2-methoximino-acetyl)-glycine ethylester (E isomer) are obtained as a brown oil of refractive index n_(D)²³ =1.4699. ##STR63##

20 g (0.12 mol) of the potassium salt of 2-cyano-2-methoximinoacetate (Eisomer) are suspended in 250 ml of dry ether, and 76.2 g (0.6 mol) ofoxalyl chloride are added dropwise at 0° C. after addition of a fewdrops of dimethylformamide. The reaction mixture is stirred at 0° C. for2 hours and filtered, and the filtrate is evaporated in vacuo at roomtemperature.

13.7 g (77% of theory) of 2-cyano-2-methoximinoacetyl chloride (Eisomer) are obtained as a yellow oil, which is immediately reactedfurther. ##STR64##

A solution of 45.1 g (0.806 mol) of potassium hydroxide in 500 ml ofwater is added dropwise to a solution of 124.8 g (0.672 mol) of 84%purity ethyl 2-cyano-2-methoximinoacetate (E isomer) in 500 ml ofethanol at 20° C., and the reaction mixture is stirred at 40° C. for onehour. The solution is evaporated in vacuo at 40° C., and the residue isstirred for 30 minutes with methanol, filtered off under suction, washedwith ethanol, acetonitrile and dichloromethane and dried at roomtemperature.

58.6 g (53% of theory) of the potassium salt of2-cyano-2-methoximino-acetate (E isomer) are obtained. ##STR65##

161 g (1.25 mols) of dimethyl sulphate (98% purity) are added dropwiseover 30 minutes to a suspension of 164 g (1 mol) of ethyl2-cyano-2-hydroximinoacetate, sodium chloride (G. Kinast, Liebigs Ann.Chem., 1981, 1561) and 138 g of powdered potassium carbonate in 1.5liters of acetone, and the reaction mixture is refluxed for 3 hours.After cooling, the mixture is filtered through kieselguhr andevaporated.

124.8 g of ethyl 2-cyano-2-methoximino-acetate (E isomer) are obtainedas a red-brown oil of 85% purity (GC). The yield is accordingly 68% oftheory. After chromatography on five times the amount of silica gel 60using chloroform, a 93% purity pale yellow oil is obtained.

The following substituted aminal derivatives of the general formula (I)are obtained in an analogous fashion and in accordance with processes(a) and (b) according to the invention:

    __________________________________________________________________________     ##STR66##                             (I)                                    Ex.                                                                           No.                                                                              R.sup.1                                                                          R.sup.2                                                                         X R.sup.3              Melting point (°C.)                     __________________________________________________________________________    2  CH.sub.3                                                                         H O C.sub.2 H.sub.5      118-20 (E-isomer)                              3  CH.sub.3                                                                         H O C.sub.3 H.sub.7 -i   145-47 (E-isomer)                              4  CH.sub.3                                                                         H O                                                                                ##STR67##           165-67 (E-isomer)                              5  CH.sub.3                                                                         H O OCH.sub.3             99-102 (E-isomer)                             6  CH.sub.3                                                                         H O OC.sub.2 H.sub.5      76-78 (E-isomer)                              7  CH.sub.3                                                                         H O NHCH.sub.3           141-42 (E-isomer)                              8  CH.sub.3                                                                         H O CH.sub.2 OCH.sub.3    89-91 (E-isomer)                              9  CH.sub.3                                                                         H O H                    130-31 (E-isomer)                              10 CH.sub.3                                                                         H O                                                                                ##STR68##           138-39 (E-isomer)                              11 CH.sub.3                                                                         H O CH.sub.2 Cl          133-35 (E-isomer)                              12 CH.sub.3                                                                         H O CH.sub.2 OCOCH.sub.3 111-13 (E-isomer)                              13 CH.sub.3                                                                         H O CHCl.sub.2           148-50 (E-isomer)                              14 CH.sub.3                                                                         H O                                                                                ##STR69##           125-27 (E-isomer)                              15 CH.sub.3                                                                         H O                                                                                ##STR70##           156-58 (E-isomer)                              16 CH.sub.3                                                                         H O COOC.sub.2 H.sub.5   95-97 (E-isomer)                               17 CH.sub.3                                                                         H O CF.sub.3             120-21 (E-isomer)                              18 CH.sub.3                                                                         H O                                                                                ##STR71##           202-05 (E-isomer)                              19 CH.sub.3                                                                         H O                                                                                ##STR72##           133-35 (E-isomer)                              20 CH.sub.3                                                                         H O CH.sub.2NHCOOC(CH.sub.3).sub.3                                                                     amorph (E-isomer)                              21 CH.sub.3                                                                         H O CH.sub.2NHCOOC.sub.2 H.sub.5                                                                       119-20 (E-isomer)                              __________________________________________________________________________

Use examples

In the following use examples, the compounds shown below are employed ascomparison substances: ##STR73## (known from DE-OS (German PublishedSpecification) 3,521,131).

EXAMPLE A

Plasmopara test (vines)/protective

Solvent: 4.7 parts by weight of acetone

Emulsifier: 0.3 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To text for protective activity, young plants are sprayed with thepreparation of active compound until dripping wet. After the spraycoating has dried on, the plants are inoculated with an aqueous sporesuspension of Plasmopara viticola and then remain in a humidity chamberat 20° to 22° C. and 100% relative atmospheric humidity for 1 day. Theplants are then placed in a greenhouse at 22° C. and about 80%atmospheric humidity for 5 days. The plants are then moistened andplaced in a humidity chamber for 1 day.

Evaluation is carried out 7 days after the inoculation.

In this test, a clearly superior activity compared with the prior art isshown, for example, by the compounds according to preparation Examples1, 2, 3, 4, 5, 6 and 7.

EXAMPLE B

Phytophthora Test (tomato)/protective

Solvent: 4.7 parts by weight of acetone

Emulsifier: 0.3 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound until dripping wet. After the spraycoating has dried on, the plants are inoculated with an aqueous sporesuspension of Phyrophthora infestans.

The plants are placed in an incubation cabin at 100% relativeatmospheric humidity and at about 20° C.

Evaluation is carried out 3 days after the inoculation.

In this test, a clearly superior activity compared with the prior art isshown, for example, by the compounds according to preparation Examples1, 2, 3, 4, 5, 6 and 7.

It will be appreciated that the instant specification and claims are setforth by way of illustration and not limitation, and that variousmodifications and changes may be made without departing from the spiritand scope of the present invention.

What is claimed is:
 1. An N,N'-diacylaminal of the formula ##STR74## inwhich R¹ stands for alkyl which is unsubstituted or substituted byhalogen, cyano, --COOR^(I), --CONR^(II) R^(III), --OR^(IV), acyl,optionally substituted aryl or optionally substituted cycloalkyl;orstands for optionally substituted alkenyl, optionally substitutedalkinyl, optionally substituted cycloalkyl, or optionally substitutedcycloalkenyl; R² stands for hydrogen or alkyl which is unsubstituted orsubstituted by cyano, alkoxy, alkylthio, --COOR^(I), acylamino,optionally substituted aryl or optionally substituted cycloalkyl;orstands for optionally substituted alkenyl, optionally substitutedalkinyl, optionally substituted cycloalkyl, optionally substitutedcycloalkenyl, or optionally substituted aryl; R³ stands for hydrogen orfor alkyl which is unsubstituted or substituted by halogen, alkoxy,alkylthio, alkylsulphinyl, alkylsulphonyl, acyloxy, acylamino, cyano,--COOR^(I), optionally substituted aryl or optionally substitutedcycloalkyl; orstands for optionally substituted alkenyl or optionallysubstituted alkinyl; or stands for optionally bridged and/or fused,optionally substituted cycloalkyl or cycloalkenyl; or stands foroptionally fused, optionally substituted aryl; or for alkoxycarbonyl,--OR⁴, --SR⁴ or --NR⁵ R⁶ ; R⁴ stands for alkyl which is unsubstituted orsubstituted by halogen, --OR^(IV), --SR^(IV), --COOR^(I), --CONR^(II)R^(III), --CN, --NR^(II) R^(III), acyl, optionally substituted aryl,optionally substituted aryloxy, optionally substituted cycloalkyl, oroptionally substituted cycloalkenyl; orstands for optionally substitutedalkenyl, optionally substituted alkinyl, optionally substitutedcycloalkyl, or cycloalkenyl; R⁵ stands for hydrogen or for alkyl whichis unsubstituted or substituted by halogen, cyano, --COOR^(I),--CONR^(II) R^(III), --NR^(II) R^(III), --OR^(IV), --S(OR_(n) R^(IV),acyl, or optionally substituted aryl, optionally substituted cycloalkyl,or cycloalkenyl; orstands for optionally substituted alkenyl, optionallysubstituted alkinyl, optionally substituted cycloalkyl, optionallysubstituted cycloalkenyl, or optionally substituted aryl; and R⁶ standsfor hydrogen or for alkyl which is unsubstituted or substituted byhalogen, cyano, --COOR^(I), --CONR^(II) R^(III), --NR^(II) R^(III),--OR^(IV), --S(O)_(n) R^(IV), acyl, or optionally substituted aryl,optionally substituted cycloalkyl, or optionally substitutedcycloalkenyl; orstands for optionally substituted alkenyl, optionallysubstituted alkinyl, optionally substituted cycloalkyl, optionallysubstituted cycloalkenyl, or optionally substituted aryl, or the--OR^(IV) group; R^(I) stands for hydrogen or alkyl which isunsubstituted or substituted by halogen, or optionally substituted aryl,optionally substituted cycloalkyl, or optionally substitutedcycloalkenyl; R^(II) and R^(III) are identical or different and standfor hydrogen or alkyl which is unsubstituted or substituted by halogen,--COOR^(IV), --CONR^(I) R^(IV), optionally substituted aryl, optionallysubstituted cycloalkyl, or optionally substituted crycloalkenyl; orstandfor alkenyl, alkinyl, optionally substituted cycloalkyl, optionallysubstituted cycloalkenyl, or optionally substituted aryl; R^(IV) standsfor hydrogen, alkyl, aralkyl, or acyl; n stands for the numbers 0, 1, or2; and X stands for oxygen or sulfur;wherein the term "optionallysubstituted aryl" stands for phenyl which is unsubstituted orsubstituted by one or more substituents independently selected from thegroup consisting of halogen, alkyl and alkoxy each having 1 to 4 carbonatoms, halogenoalkyl and halogenoalkoxy each having 1 to 2 differentcarbon atoms and 1 to 5 identical or different halogen atoms; the term"optionally substituted aryloxy" stands for "optionally substitutedaryl" bonded through oxygen; the terms "optionally substitutedcycloalkyl" and "optionally substituted cycloalkenyl" stand forcycloalkyl and cycloalkenyl which are each unsubstituted or substitutedby alkyl having 1 to 4 carbon atoms; the terms "optionally substitutedalkenyl" and "optionally substituted alkinyl" stand for alkenyl oralkinyl which are each unsubstituted or substituted by phenyl which isunsubstituted or substituted by a substituent selected from the groupconsisting of halogen and alkyl having 1 to 4 carbon atoms; the term"optionally bridged and/or fused optionally substituted cycloalkyl orcycloalkenyl" stands for cycloalkyl or cycloalkenyl each of which is (1)unbridged or bridged by methylene or ethylene, (2) unfused or fused to 1or 2 benzene, cyclopentane, or cyclohexane rings, and (3) unsubstitutedor substituted by one or more substituents independently selected fromthe group consisting of halogen, alkyl and alkoxy each having 1 to 4carbon atoms, acyloxy and acylamino each having 2 to 5 carbon atoms, theoxo group, phenyl, hydroxycarbonyl, and alkoxycarbonyl having 1 to 4carbon atoms in the alkoxy part; and the term "optionally fused,optionally substituted aryl" stands for phenyl which is (1) unfused orfused to 1 to 2 benzene or cyclohexane rings and (2) unsubstituted orsubstituted by one or more substituents independently selected from thegroup consisting of halogen, hydroxyl, nitro, alkyl and alkoxy eachhaving 1 to 4 carbon atoms, halogenoalkyl and halogenoalkoxy each having1 to 2 carbon atoms and 2 to 5 identical or different halogen atoms,acylamino and acylalkylamino each having 2 to 5 carbon atoms in the acylpart and 1 to 4 carbon atoms in the alkyl part, hydroxycarbonyl andalkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy part.
 2. AnN,N'-diacylaminal according to claim 1, in whichR¹ stands forstraight-chain or branched alkyl having 1 to 6 carbon atoms which isunsubstituted or monosubstituted to pentasubstituted by identical ordifferent substituents selected from the group consisting of (i)fluorine, chlorine, bromine, iodine, cyano, --COOR^(I), --CONR^(II)R^(III), --OR^(IV), acyl having 2 to 9 carbon atoms, phenyl which isunsubstituted or monosubstituted to pentasubstituted by identical ordifferent substituents selected from the group consisting of (ii)halogen, alkyl and alkoxy each having 1 to 4 carbon atoms, halogenoalkyland halogenoalkoxy each having 1 to 2 carbon atoms and 1 to 5 identicalor different halogen atoms; or (i) cycloalkyl having 3 to 6 carbon atomswhich is unsubstituted or monosubstituted to pentasubstituted byidentical or different (ii) alkyl having 1 to 4 carbon atoms; R² standsfor hydrogen or straight-chain or branched alkyl having 1 to 5 carbonatoms which is unsubstituted or monosubstituted to pentasubstituted byidentical or different substituents (i) selected from the groupconsisting of cyano, alkoxy and alkylthio, each having 1 to 4 carbonatoms, --COOR¹, acylamino having 2 to 9 carbon atoms, phenyl which isunsubstituted or monosubstituted to pentasubstituted by identical ordifferent substituents (ii) halogen, alkyl and alkoxy each having 1 to 4carbon atoms, halogenoalkyl and halogenoalkoxy each having 1 or 2 carbonatoms and 1 to 5 identical or different halogen atoms, and (i)cycloalkyl having 3 to 6 carbon atoms which is unsubstituted ormonosubstituted to pentasubstituted by identical or different (ii) alkylhaving 1 to 4 carbon atoms; orstands for phenyl which is unsubstitutedor monosubstituted to pentasubstituted by identical substituents (i)halogen, alkyl and alkoxy each having 1 to 4 carbon atoms, halogenoalkyland halogenoalkoxy each having 1 or 2 carbon atoms and 1 to 5 identicalor different halogen atoms; R³ stands for hydrogen or straight-chain orbranched alkyl having 1 to 6 carbon atoms which is unsubstituted ormonosubstituted to pentasubstituted by identical or differentsubstituents (i) selected from the group consisting of fluorine,chlorine, bromine, iodine, cyano, alkoxy, alkylthio, alkylsulphinyl andalkylsulphonyl each having 1 to 4 carbon atoms, acyloxy and acylaminoeach having 2 to 9 carbon atoms, --COOR^(I), phenyl which isunsubstituted or monosubstituted to pentasubstituted by identical ordifferent substituents (ii) halogen, alkyl and alkoxy each having 1 to 4carbon atoms, halogenoalkyl and halogenoalkoxy each having 1 or 2 carbonatoms and 1 to 5 identical or different halogen atoms, or (i) cycloalkylhaving 3 to 6 carbon atoms which is unsubstituted on monosubstituted topentasubstituted by identical or different (ii) alkyl having 1 to 4carbon atoms; orstands for cycloalkyl having 3 to 6 carbon atoms orcycloalkenyl having 5 to 7 carbon atoms, each of which is unbridged orbridged by methylene or ethylene, unfused or fused to 1 or 2 benzene,cyclopentane or cyclohexane rings, and unsubstituted or monosubstitutedto pentasubstituted by identical or different substituents (i) selectedfrom the group consisting of halogen, alkyl and alkoxy each having 1 to4 carbon atoms, acyloxy and acylamino each having 2 to 5 carbon atoms,the oxo group, phenyl, hydroxycarbonyl and alkoxycarbonyl having 1 to 4carbon atoms in the alkoxy part; or stands for phenyl which is unfusedor fused to 1 or 2 benzene or cyclohexane rings and unsubstituted ormonosubstituted to pentasubstituted by identical or differentsubstituents (i) selected from the group consisting of halogen,hydroxyl, nitro, alkyl and alkoxy each having 1 to 4 carbon atoms,halogenoalkyl and halogenoalkoxy each having 1 or 2 carbon atoms and 2to 5 identical or different halogen atoms, acylamino and acylalkylaminoeach having 2 to 5 carbon atoms in the acyl part and 1 to 4 carbon atomsin the alkyl part, hydroxycarbonyl, and alkoxycarbonyl having 1 to 4carbon atoms in the alkoxy part, or stands for alkoxycarbonyl having 1to 4 carbon atoms in the alkoxy part, or for --OR⁴, --SR⁴ or --NR⁵ R⁶ ;or R¹, R² and R³ independently of one another stand for straight-chainor branched alkenyl or alkinyl, each of which has 2 to 6 carbon atoms isunsubstituted or monosubstituted to trisubstituted by identical ordifferent substituents selected from the group consisting of (i) phenylwhich is unsubstituted or monosubstituted to pentasubstituted byidentical or different substituents selected from the group consistingof (ii) halogen and alkyl having 1 to 4 carbon atoms; X stands foroxygen or sulfur;wherein R⁴ stands for straight-chain or branched alkylhaving 1 to 6 carbon atoms which is unsubstituted or monosubstituted topentasubstituted by identical or different substituents (i) selectedfrom the group consisting of halogen, --OR^(IV), --SR^(IV), --COOR^(I),--CONR^(II) R^(III), CN, --NR^(II) R^(III), acyl having 2 to 9 carbonatoms, phenyl or phenoxy, each of which is unsubstituted ormonosubstituted to pentasubstituted by identical or differentsubstituents (ii) selected from the group consisting of halogen andalkyl having 1 to 4 carbon atoms, and (i) cycloalkyl having 3 to 6carbon atoms or cycloalkenyl having 5 to 7 carbon atoms, each of whichis unsubstituted or monosubstituted to pentasubstituted by identical ordifferent (ii) alkyl having 1 to 4 carbon atoms; orstands for alkenyl oralkinyl each having 2 to 6 carbon atoms, or for cycloalkyl having 3 to 6carbon atoms or cycloalkenyl having 5 to 7 carbon atoms, each of whichis unsubstituted or monosubstituted to pentasubstituted by identical ordifferent (i) alkyl having 1 to 4 carbon atoms; R⁵ stands for hydrogenor for straight-chain or branched alkyl having 1 to 4 carbon atoms whichis unsubstituted or monosubstituted or disubstituted by identical ordifferent substituents (i) selected from the group consisting ofhalogen, --cyano, --COOR^(I), --CONR^(II) _(R) ^(III), --NR^(II)R^(III), --OR^(IV), --S(O)_(n) R^(IV), acyl having 2 to 9 carbon atoms,phenyl, which is unsubstituted or monosubstituted to pentasubstituted byidentical or different substituents (ii) selected from the groupconsisting of halogen and alkyl having 1 to 4 carbon atoms, and (i)cycloalkyl having 3 to 6 carbon atoms or cycloalkenyl having 5 to 7carbon atoms, each of which is unsubstituted or monosubstituted topentasubstituted by identical or different (ii) alkyl having 1 to 4carbon atoms; orstands for straight-chain or branched alkenyl or alkinyleach having 2 to 6 carbon atoms, for cycloalkenyl having 5 to 7 carbonatoms, which is unsubstituted or monosubstituted to pentasubstituted byidentical or different (i) alkyl having 1 to 4 carbon atoms; or forcycloalkyl having 3 to 6 carbon atoms which is unsubstituted ormonosubstituted to pentasubstituted by identical or differentsubstituents (i) selected from the group consisting of halogen, alkyland alkoxy each having 1 to 4 carbon atoms, cyano, amino, carbamoyl,alkylamino, dialkylamino, alkylcarbamoyl and dialkylcarbamoyl eachhaving 1 to 4 carbon atoms in each alkyl part, alkoxycarbonylaminohaving 1 to 4 carbon atoms in the alkoxy part, cycloalkyl andcycloalkylalkyl having 5 or 6 carbon atoms in the cycloalkyl part and 1to 4 carbon atoms in the straight-chain or branched alkyl part, orphenyl which is optionally unsubstituted or monosubstituted topentasubstituted by identical or different substituents (ii) from thegroup consisting of halogen and alkyl having 1 to 4 carbon atoms; orstands for phenyl which is unsubstituted or monosubstituted topentasubstituted by identical or different substituents (i) from thegroup consisting of halogen, alkyl or alkoxy each having 1 to 4 carbonatoms, or halogenoalkyl or halogenalkoxy each having 1 or 2 carbon atomsand 1 to 5 identical or different halogen atoms; R⁶ stands for themeanings of R⁵ or the --OR^(IV) group;wherein R^(I) stands for hydrogenor straight-chain or branched alkyl having 1 to 6 carbon atoms; R^(II)and R^(III) independently of one another stand for hydrogen,straight-chain or branched alkyl having 1 to 6 carbon atoms, phenylalkylwhich has 1 to 4 carbon atoms in the straight-chain or branched alkylpart and is unsubstituted or monosubstituted to pentasubstituted on thephenyl by identical or different substituents (i) selected from thegroup consisting of halogen, alkyl or alkoxy each having 1 to 4 carbonatoms, or halogenoalkyl or halogenoalkoxy each having 1 or 2 carbonatoms and 2 to 5 identical or different halogen atoms; orstand foralkoxycarbonylalkyl, carbamoylalkyl, alkylcarbamoylalkyl ordialkylcarbonylalkyl each having 1 to 4 carbon atoms in each alkyl part,or for cycloalkyl having 3 to 6 carbon atoms which is unsubstituted orsubstituted by straight-chain or branched (i) alkyl having 1 to 4 carbonatoms; R^(IV) stands for hydrogen, straight-chain or branched alkylhaving 1 to 6 carbon atoms, phenylalkyl which has 1 to 4 carbon atoms inthe straight-chain or branched alkyl part and is unsubstituted ormonosubstituted to pentasubstituted on the phenyl by identical ordifferent substituents (i) selected from the group consisting ofhalogen, alkyl or alkoxy each having 1 to 4 carbon atoms, orhalogenoalkyl or halogenoalkoxy each having 1 or 2 carbon atoms and 2 to5 identical or different halogen atoms; orstands for acyl having 2 to 9carbon atoms; and n stands for the numbers 0, 1 or
 2. 3. AnN,N'-diacylaminal according to claim 1, in whichstands forstraight-chain or branched alkyl having 1 to 4 carbon atoms which isunsubstituted or monosubstituted to trisubstituted by identical ordifferent substituents (i) selected from the group consisting offluorine, chlorine, bromine, iodine, cyano, --COOR^(I), --CONR^(II)RIII, --OR^(IV), acyl having 2 to 9 carbon atoms, phenyl which isunsubstituted or monosubstitited to trisubstituted by identical ordifferent substituents (ii) selected from the group consisting offluorine, chlorine, methyl and methoxy; or (i) cyclopropyl orcyclohexyl, each of which is unsubstituted or monosubstituted totrisubstituted by (ii) methyl; orstands for allyl or propargyl each ofwhich is unsubstituted or monosubstituted or disubstituted by methyl; R²stands for hydrogen or straight-chain or branched alkyl having 1 to 4carbon atoms which is unsubstituted or monosubstituted to trisubstitutedby identical or different substituents (i) selected from the groupconsisting of cyano, methoxy, ethoxy, methylthio, ethylthio, --COOR^(I),acylamino having 2 to 9 carbon atoms, phenyl which is unsubstituted ormonosubstituted to trisubstituted by identical or different substituents(ii) from the group consisting of halogen, methyl, or methoxy, or (i)cyclopropyl or cyclohexyl, each of which is unsubstituted ormonosubstituted to trisubstituted by (ii) methyl; orstands for allyl,allenyl, vinyl, propargyl or ethinyl, each of which is unsubstituted orsubstituted by (i) phenyl which is unsubstituted or monosubstituted totrisubstituted by identical or different substituents (ii) from thegroup consisting of halogen and methyl; or stands for phenyl which isunsubstituted or monosubstituted to trisubstituted by identicalsubstituents (i) from the group consisting of halogen, methyl, andmethoxy; R³ stands for hydrogen or straight-chain or branched alkylhaving 1 to 4 carbon atoms which is unsubstituted or monosubstituted totrisubstituted by identical or different substituents (i) selected fromthe group consisting of fluorine, chlorine, bromine, iodine, cyano,alkoxy, alkylthio, alkylsulphinyl and alkylsulphonyl each having 1 or 2carbon atoms, acyloxy and acylamino each having 2 to 9 carbon atoms,--COOR^(I), cyclopropyl, cyclopentyl, cyclohexyl or phenyl which isunsubstituted or monosubstituted to trisubstituted by identical ordifferent substituents (ii) from the group consisting of halogen andmethyl; orstands for vinyl or ethinyl, each of which is unsubstituted orsubstituted by (i) phenyl which is unsubstituted or monosubstituted totrisubstituted by identical or different substituents (ii) from thegroup consisting of halogen and methyl, or by (i) methyl; or stands forcyclopropyl, cyclopentyl, cyclohexyl, cyclopentenyl, or cyclohexenyl,each of which is unbridged or bridged by methylene or ethylene, unfusedor fused to 1 or 2 benzene, cyclopentane or cyclohexane rings, andunsubstituted or monosubstituted to trisubstituted by identical ordifferent substituents (i) selected from the group consisting ofhalogen, methyl, methoxy, acyloxy and acylamino each having 2 to 5carbon atoms, the oxo group, phenyl, hydroxycarbonyl, methoxycarbonyland ethoxycarbonyl; or stands for phenyl which is unfused or fused to 1or 2 benzene or cyclohexane rings and unsubstituted or monosubstitutedto trisubstituted by identical or different substituents (i) selectedfrom the group consisting of fluorine, chlorine, hydroxyl, nitro,methyl, methoxy, acylamino and N-alkylacylamino each having 2 to 5carbon atoms in the acyl part and 1 or 2 carbon atoms in the alkoxypart, hydroxycarbonyl, methoxycarbonyl and ethoxycarbonyl; or stands foralkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy part, or for--OR⁴, --SR⁴ or --NR⁵ R⁶ ; X stands for oxygen or sulfur;wherein R⁴stands for straight-chain or branched alkyl having 1 to 4 carbon atomswhich is unsubstituted or monosubstituted to trisubstituted by identicalor different substituents (i) selected from the group consisting offluorine, chlorine, --OR^(IV), --SR^(IV), --COOR^(I), --CONR^(II)R^(III), CN, --NR^(II) R^(III), alkylcarbonyl having 1 to 4 carbon atomsin the straight-chain or branched alkyl part, phenyl or phenoxy, each ofwhich is unsubstituted or monosubstituted to trisubstituted by identicalor different substituents (ii) selected from the group consisting ofhalogen and methyl, or (i) cyclopropyl, cyclohexyl, cyclopentenyl orcyclohexenyl, each of which is unsubstituted or monosubstituted totrisubstituted by (ii) methyl; orstands for allyl or propargyl, each ofwhich is unsubstituted or monosubstituted or disubstituted by (i)methyl; or for cyclopropyl, cyclohexyl, cyclopentenyl or cyclohexenyl,each of which is unsubstituted or monosubstituted to trisubstituted by(ii) methyl; R⁵ stands for hydrogen or for straight-chain or branchedalkyl having 1 to 4 carbon atoms which is unsubstituted ormonosubstituted or disubstituted by identical or different substituents(i) selected from the group consisting of halogen, cyano, --COOR^(I),--CONR^(II) R^(III), CN, --NR^(II) R^(III), OR^(IV), --S(O)_(n) R^(IV),acyl having 2 to 9 carbon atoms, phenyl, which is unsubstituted ormonosubstituted to trisubstituted by identical or different substituents(ii) selected from the group consisting of halogen and alkyl having 1 to4 carbon atoms, or (i) cycloalkyl having 3 to 6 carbon atoms orcycloalkenyl having 5 to 7 carbon atoms, each of which is unsubstitutedor substituted by (ii) straight-chain or branched alkyl having 1 to 4carbon atoms; orstands for straight-chain or branched alkenyl or alkinyleach having 2 to 6 carbon atoms, for cycloalkenyl having 5 to 7 carbonatoms, which is unsubstituted or substituted by straight-chain orbranched (i) alkyl having 1 to 4 carbon atoms; or for cycloalkyl having3 to 6 carbon atoms which is unsubstituted or substituted by (i)halogen, straight-chain or branched alkyl and alkoxy each having 1 to 4carbon atoms, cyano, amino, carbamoyl, in each case straight-chain orbranched alkylamino, dialkylamino, alkylcarbamoyl and dialkylcarbamoyleach having 1 to 4 carbon atoms in each alkyl part, alkoxycarbonylaminohaving 1 to 4 carbon atoms in the straight-chain or branched alkoxypart, cycloalkyl and cycloalkylalkyl having 5 or 6 carbon atoms in thecycloalkyl part and 1 to 4 carbon atoms in the straight-chain orbranched alkyl part, or phenyl, which is unsubstituted ormonosubstituted to trisubstituted by identical or different substituents(ii) from the group consisting of halogen and alkyl having 1 to 4 carbonatoms; or stands for phenyl which is unsubstituted or monosubstituted totrisubstituted by identical or different substituents (i) from the groupconsisting of halogen, straight-chain or branched alkyl or alkoxy eachhaving 1 to 4 carbon atoms, or halogenoalkyl or halogenalkoxy eachhaving 1 or 2 carbon atoms and 1 to 5 identical or different halogenatoms; R⁶ stands for the meanings of R⁵ or the --OR^(IV) group;whereinR^(I) stands for hydrogen or straight-chain or branched alkyl having 1to 4 carbon atoms; R^(II) and R^(III) independently of one another standfor hydrogen, straight-chain or branched alkyl having 1 to 4 carbonatoms, or benzyl or phenethyl each of which is unsubstituted ormonosubstituted to trisubstituted on the phenyl by identical ordifferent substituents (i) selected from the group consisting offluorine, chlorine, methyl, methoxy and trifluoromethyl; orstand foralkoxycarbonylalkyl having 1 to 4 carbon atoms in the alkoxy part and 1or 2 carbon atoms in the alkyl part, carbamoylalkyl, alkylcarbamoylalkylor dialkylcarbonylalkyl each having 1 or 2 carbon atoms in each alkylpart, or for cycloalkyl having 3 to 6 carbon atoms which isunsubstituted or monosubstituted to trisubstituted by identical ordifferent substituents selected from the group consisting of methyl andethyl; R^(IV) stands for hydrogen, straight-chain or branched alkylhaving 1 to 4 carbon atoms, or benzyl or phenethyl each of which isunsubstituted or monosubstituted to trisubstituted on the phenyl byidentical or different substituents selected from the group consistingof fluorine, chlorine, methyl, methoxy and trifluoromethyl; orstands foracyl having 2 to 9 carbon atoms; and n stands for the numbers 0, 1 or 2.4. An N,N'-diacylaminal according to claim 1, in whichR¹ stands forstraight-chain or branched alkyl having 1 or 2 carbon atoms which isunsubstituted or monosubstituted to trisubstituted by identical ordifferent substituents selected from the group consisting of (i)fluorine, chlorine, cyano, --COOR^(I), --CONR^(II) R^(III), --OR^(IV),alkylcarbonyl having 1 to 4 carbon atoms in the straight-chain orbranched alkyl part, phenyl which is unsubstituted or monosubstitited totrisubstituted by identical or different substituents (ii) selected fromthe group consisting of fluorine, chlorine and methyl; or (i)cyclopropyl or cyclohexyl, each of which is unsubstituted ormonosubstituted to trisubstituted by (ii) methyl; orstands for allyl orpropargyl; R² stands for hydrogen or for alkyl having 1 to 4 carbonatoms which is unsubstituted or monosubstituted or disubstituted byidentical or different substituents (i) selected from the groupconsisting of cyano, methoxy, ethoxy, methylthio, ethylthio, --COOR^(I),alkylcarbonylamino having 1 to 4 carbon atoms in the straight-chain orbranched alkyl part, phenyl which is unsubstituted or monosubstituted totrisubstituted by identical or different substituents (ii) from thegroup consisting of halogen, methyl, or methoxy, or (i) cyclopropyl orcyclohexyl, each of which is unsubstituted or monosubstituted totrisubstituted by (ii) methyl; orstands for allyl, allenyl, vinyl,propargyl or ethinyl, each of which is unsubstituted or substituted by(i) phenyl which may be unsubstituted or monosubstituted totrisubstituted by identical or different substituents (ii) from thegroup consisting of halogen and methyl; or stands for phenyl which isunsubstituted or monosubstituted to trisubstituted by identicalsubstituents (i) from the group consisting of halogen, methyl, andmethoxy; R³ stands for hydrogen or straight-chain or branched alkylhaving 1 to 4 carbon atoms which is unsubstituted or monosubstituted ordisubstituted by identical or different substituents (i) selected fromthe group consisting of fluorine, chlorine, bromine, iodine, cyano,alkoxy, alkylthio, alkylsulphinyl and alkylsulphonyl each having 1 or 2carbon atoms, alkylcarbonyloxy having 1 to 4 carbon atoms in thestraight-chain or branched alkyl part, formamido, alkylcarbonylaminohaving 1 or 2 carbon atoms in the alkyl part, which is unsubstituted orsubstituted by (ii) fluorine, (i) benzoylamino which is unsubstituted orsubstituted by (ii) chlorine, (i) alkoxycarbonylamino having 1 to 4atoms in the straight-chain or branched alkoxy part, --COOR^(I),cyclopropyl, cyclopentyl, cyclohexyl or phenyl which is unsubstituted ormonosubstituted to trisubstituted by identical or different substituents(ii) from the group consisting of halogen and methyl; orstands for vinylor ethinyl, each of which is unsubstituted or monosubstituted ordisubstituted by identical or different substituents selected from thegroup consisting of (i) phenyl which is unsubstituted or monosubstitutedto trisubstituted by identical or different substituents (ii) from thegroup consisting of halogen and methyl, or by (i) methyl; or stands forcyclopropyl, cyclopentyl, cyclohexyl, cyclopentenyl, or cyclohexenyl,each of which is unbridged or bridged by methylene or ethylene, unfusedor fused to 1 or 2 benzene, cyclopentane or cyclohexane rings, andunsubstituted or monosubstituted to trisubstituted by identical ordifferent substituents (i) selected from the group consisting ofhalogen, methyl, the oxo group, phenyl, hydroxycarbonyl, methoxycarbonyland ethoxycarbonyl; or stands for phenyl which is unfused or fused to 1or 2 benzene or cyclohexane rings and is unsubstituted ormonosubstituted to trisubstituted by identical or different substituents(i) selected from the group consisting of fluorine, chlorine, hydroxyl,nitro, methyl, methoxy, acetoxy, acetamido, hydroxycarbonyl,methoxycarbonyl and ethoxycarbonyl; or stands for alkoxycarbonyl having1 to 4 carbon atoms in the alkoxy part, or for --OR⁴, --SR⁴ or --NR⁵ R⁶; X stands for oxygen or sulfur;wherein R⁴ stands for straight-chain orbranched alkyl having 1 or 2 carbon atoms which is unsubstituted ormonosubstituted or disubstituted by identical or different substituents(i) selected from the group consisting of fluorine, chlorine, methoxy,ethoxy, methylthio, alkoxycarbonyl having 1 to 4 carbon atoms in thestraight-chain or branched alkoxy part, carbamoyl, methylcarbamoyl,dimethylcarbamoyl, cyano, dimethylamino, diethylamino, acetyl, pivaloyl,or phenyl or phenoxy, each of which is unsubstituted or monosubstitutedto trisubstituted by identical or different substituents (ii) selectedfrom the group consisting of halogen and methyl, or (i) cyclopropyl orcyclohexyl, each of which is unsubstituted or monosubstituted totrisubstituted by (ii) methyl; orstands for allyl or propargyl, each ofwhich is unsubstituted or monosubstituted or disubstituted by (i)methyl; or for cyclohexyl which is unsubstituted or monosubstituted totrisubstituted by (i) methyl; R⁵ stands for hydrogen or forstraight-chain or branched alkyl having 1 to 4 carbon atoms or alkylhaving 1 to 3 carbon atoms which is monosubstituted or disubstituted byidentical or different substituents (i) selected from the groupconsisting of chlorine, hydroxyl, alkylcarbonyloxy having 1 to 4 carbonatoms in the straight-chain or branched alkyl part, alkylcarbonyl having1 to 4 carbon atoms in the straight-chain or branched alkyl part, alkoxyand alkylthio each having 1 or 2 carbon atoms, alkoxycarbonyl having 1to 4 carbon atoms in the straight-chain or branched alkoxy part,carbamoyl, methylcarbamoyl, dimethylcarbamoyl, cyano, dimethylamino,diethylamino, cyclopropyl, cyclohexyl or phenyl, which is unsubstitutedor monosubstituted to trisubstituted by identical or differentsubstituents (ii) selected from the group consisting of chlorine andmethyl; orstands for allyl or propargyl, for 1-cyclohexenyl, or forcyclohexyl which is unsubstituted or monosubstituted to trisubstitutedby identical or different substituents (i) from the group consisting ofchlorine, methyl, ethyl, methoxy, cyano, amino, alkylamino,dialkylamino, alkylcarbamoyl and dialkylcarbamoyl each having 1 or 2carbon atoms in each alkyl part, cyclohexyl or cyclohexylalkyl having 1or 2 carbon atoms in the alkyl part; or stands for phenyl which isunsubstituted or monosubstituted to trisubstituted by identical ordifferent substituents (i) from the group consisting of chlorine andmethyl; R⁶ stands for the meanings of R⁵ or the --OR^(IV) group;whereinR^(I) stands for methyl, ethyl, n- or i-propyl and n-, i-, s- ort-butyl; R^(II) and R^(III) independently of one another stand forhydrogen, methyl, ethyl, n- or i-propyl, for benzyl which isunsubstituted or monosubstituted to trisubstituted on the phenyl byidentical or different substituents (i) selected from the groupconsisting of chlorine and methyl; orstand for alkoxycarbonylalkylhaving 1 or 2 carbon atoms in the alkoxy part and 1 or 2 carbon atoms inthe alkyl part, carbamoylalkyl, alkylcarbamoylalkyl ordialkylcarbonylalkyl each having 1 or 2 carbon atoms in each alkyl part,or for cyclohexyl which is unsubstituted or monosubstituted totrisubstituted by (i) methyl; and R^(IV) stands for hydrogen, alkylhaving 1 or 2 carbon atoms, or benzyl which is unsubstituted ormonosubstituted to trisubstituted on the phenyl by identical ordifferent substituents (i) selected from the group consisting offluorine, chlorine, and methyl.
 5. AnN-(2-cyano-2-oximino-acetyl)-aminal of the formula ##STR75## in which R¹stands for alkyl which is unsubstituted or substituted by halogen,cyano, --COOR^(I), --CONR^(II) R^(III), --OR^(IV), acyl, optionallysubstituted aryl or optionally substituted cycloalkyl; orstands foroptionally substituted alkenyl, optionally substituted alkinyl,optionally substituted cycloalkyl, or optionally substitutedcycloalkenyl; R² stands for hydrogen or alkyl which is unsubstituted orsubstituted by cyano, alkoxy, alkylthio, --COOR^(I), acylamino,optionally substituted aryl or optionally substituted cycloalkyl;orstands for optionally substituted alkenyl, optionally substitutedalkinyl, optionally substituted cycloalkyl, optionally substitutedcycloalkenyl, or optionally substituted aryl; R^(I) stands for hydrogenor alkyl which is unsubstituted or substituted by halogen, or optionallysubstituted aryl, optionally substituted cycloalkyl, or optionallysubstituted cycloalkenyl; R^(II) and R^(III) are identical or differentand stand for hydrogen or alkyl which is unsubstituted or substituted byhalogen, --COOR^(IV), --CONR^(I) R^(IV), optionally substituted aryl,optionally substituted cycloalkyl, or optionally substitutedcycloalkenyl; orstand for alkenyl, alkinyl, optionally substitutedcycloalkyl, optionally substituted cycloalkenyl, or optionallysubstituted aryl; R^(IV) stands for hydrogen, alkyl, aralkyl, or acyl;and HY stands for the equivalent of an inorganic or organic acid;whereinthe term "optionally substituted aryl" stands for phenyl which isunsubstituted or substituted by one or more substituents independentlyselected from the group consisting of halogen, alkyl and alkoxy eachhaving 1 to 4 carbon atoms, halogenoalkyl and halogenoalkoxy each having1 or 2 different carbon atoms and 1 to 5 identical or different halogenatoms;the terms "optionally substituted cycloalkyl" and "optionallysubstituted cycloalkenyl" stand for cycloalkyl and cycloalkenyl whichare each unsubstituted or substituted by alkyl having 1 to 4 carbonatoms; and the terms "optionally substituted alkenyl" and "optionallysubstituted alkinyl" stand for alkenyl or alkinyl which are eachunsubstituted or substituted by phenyl which is unsubstituted orsubstituted by a substituent selected from the group consisting ofhalogen and alkyl having 1 to 4 carbon atoms.
 6. An isocyanate of theformula ##STR76## in which R¹ stands for alkyl which is unsubstituted orsubstituted by halogen, cyano, --COOR^(I), --CONR^(II) R^(III),--OR^(IV), acyl, optionally substituted aryl or optionally substitutedcycloalkyl; orstands for optionally substituted alkenyl, optionallysubstituted alkinyl, optionally substituted cycloalkyl, or optionallysubstituted cycloalkenyl; R² stands for hydrogen or alkyl which isunsubstituted or substituted by cyano, alkoxy, alkylthio, --COOR^(I),acylamino, optionally substituted aryl or optionally substitutedcycloalkyl; orstands for optionally substituted alkenyl, optionallysubstituted alkinyl, optionally substituted cycloalkyl, optionallysubstituted cycloalkenyl, or optionally substituted aryl; R^(I) standsfor hydrogen or alkyl which is unsubstituted or substituted by halogen,or optionally substituted aryl, optionally substituted cycloalkyl, oroptionally substituted cycloalkenyl; R^(II) and R^(III) are identical ordifferent and stand for hydrogen or alkyl which is unsubstituted orsubstituted by halogen, --COOR^(IV), --CONR^(I) R^(IV), optionallysubstituted aryl, optionally substituted cycloalkyl, or optionallysubstituted cycloalkenyl; orstand for alkenyl, alkinyl, optionallysubstituted cycloalkyl, optionally substituted cycloalkenyl, oroptionally substituted aryl; R^(IV) stands for hydrogen, alkyl, aralkyl,or acyl;wherein the term "optionally substituted aryl" stands for phenylwhich is unsubstituted or substituted by one or more substituentsindependently selected from the group consisting of halogen, alkyl andalkoxy each having 1 to 4 carbon atoms, halogenoalkyl and halogenoalkoxyeach having 1 or 2 different carbon atoms and 1 to 5 identical ordifferent halogen atoms; the terms "optionally substituted cycloalkyl"and "optionally substituted cycloalkenyl" stand for cycloalkyl andcycloalkenyl which are each unsubstituted or substituted by alkyl having1 to 4 carbon atoms; and the terms "optionally substituted alkenyl" and"optionally substituted alkinyl" stands for alkenyl or alkinyl which areeach unsubstituted or substituted by phenyl which is unsubstituted orsubstituted by a substituent selected from the group consisting ofhalogen and alkyl having 1 to 4 carbon atoms.
 7. A compound according toclam 1, wherein such compound isN-acetamidomethyl-(E)-2-cyano-2-methoximinoacetamide of the formula##STR77##
 8. A compound according to claim 1, wherein such compound isN-propionylamidomethyl-(E)-2-cyano-2-methoximinoacetamide of the formula##STR78##
 9. A compound according to claim 1, wherein such compound isN-benzoylamidomethyl-(E)-2-cyano-2-methoximinoacetamide of the formula##STR79##
 10. A compound according to claim 1, wherein such compound isN-methoxycarbonylamidomethyl-(E)-2-cyanomethoximinoacetamide of theformula ##STR80##
 11. A compound according to claim 1, wherein suchcompound is N-ethoxycarbonylamidomethyl-(E)-2-cyanomethoximinoacetamideof the formula ##STR81##
 12. A fungicidal composition comprising afungicidally effective amount of a compound according to claim 1 and adiluent.
 13. A method of combating fungi which comprises applying tosuch fungi or to a fungus habitat a fungicidally effective amount of acmpound according to claim
 1. 14. The method according to claim 13,wherein such compoundisN-acetamidomethyl-(E)-2-cyano-2-methoximinoacetamide,N-propionylamidomethyl-(E)-2-cyano-2-methoximinoacetamide,N-benzoylamidomethyl-(E)-2-cyano-2-methoximinoacetamide,N-methoxycarbonylamidomethyl-(E)-2-cyanomethoximinoacetamide, orN-ethoxycarbonylamidomethyl-(E)-2-cyanomethoximinoacetamide.